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palmitoleyl alcohol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
With pyridinium chlorochromate In dichloromethane at 20℃; for 2h; | 98% |
With pyridinium chlorochromate In dichloromethane for 1.5h; Ambient temperature; | 94% |
With pyridinium chlorochromate | 94% |
(Z)-4-undecene-1-ol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 2: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 3: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 4: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme |
(Z)-4-undecenal
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 2: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 3: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 4: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 5: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme |
(Z)-4-undecenyl bromide
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 2: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 3: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme |
1,1-dimethoxy-8-tosyloxy-(4Z)-octene
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: 63 percent / dilithium tetrachlorocuprate / tetrahydrofuran / 1.) -78 deg C, 2 h, 2.) RT, 15 h 2: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 3: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 4: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 5: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 6: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 7: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme |
1,1-dimethoxy-(4Z)-undecene
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 99 percent / 5percent HCl / acetone / 6 h / Ambient temperature 2: 95 percent / diisobutylaluminum hydride / diethyl ether; toluene / 1.5 h / -10 °C 3: 96 percent / triphenylphosphine, Br2 / CCl4 / 16 h / Ambient temperature 4: 1.) cuprous iodide, 2,2' bipyridyl / 1.) THF, 2 deg C, 10 min, 2.) THF, a) 2 deg C, 2 h, b) RT, 15 h 5: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 6: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme |
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: p-toluenesulfonic acid / methanol; H2O / 15 h / 20 °C 2: 94 percent / pyridinium chlorochromate / CH2Cl2 / 1.5 h / Ambient temperature View Scheme |
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 2.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 2.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 3.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 4.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme |
(Z)-9-hexadecenoic acid methyl ester
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 2: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme | |
Multi-step reaction with 2 steps 1: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 2: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme | |
With 1-methyl-piperazine; sodium bis(2-methoxyethoxy)aluminium dihydride In toluene at 20℃; for 2h; Sealed tube; Inert atmosphere; Cooling with ice; |
methyl ester of azelaic acid aldehyde
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 3.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 2: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 3: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme |
triphenylheptylphosphonium bromide
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 1.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 2.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 3.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h 2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 3: 67 percent / pyridinium chlorochromate / CH2Cl2 / 0.67 h / 20 °C View Scheme |
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1.1: 97.95 percent / aq. H2SO4 / 0.11 h / microwave irradiation 2.1: 60.91 percent / aq. NaIO4 / acetonitrile / 0.5 h / 5 °C 3.1: sodium amide / tetrahydrofuran; hexamethylphosphoric acid triamide / 1.5 h / 20 °C 3.2: 91.52 percent / tetrahydrofuran; hexamethylphosphoric acid triamide / -73 - 20 °C 4.1: 92 percent / lithium aluminum hydride / tetrahydrofuran / 2 h / 0 °C 5.1: 66.64 percent / pyridinium chlorochromate / CH2Cl2 / 3 h / 20 °C View Scheme |
8-Bromo-1-octene
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 4: 94 percent / PCC View Scheme |
1-octynyllithium
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 87 percent / NH3 2: 1) 9-BBN, 2) H2O2, AcONa 3: 88 percent / H2 / Ni-P2 4: 94 percent / PCC View Scheme |
9-hexadecyn-1-ol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 88 percent / H2 / Ni-P2 2: 94 percent / PCC View Scheme | |
Multi-step reaction with 2 steps 1: H2 / Cu/γ-Al2O3 / 3.33 h / 119.9 °C / 60004.8 Torr / other supported catalyst; other time; stereoselective hydrogenation of C16 acetylenic alcohols on supported copper catalyst View Scheme | |
Multi-step reaction with 2 steps 1: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 2: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme |
hexadec-1-en-9-yne
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) 9-BBN, 2) H2O2, AcONa 2: 88 percent / H2 / Ni-P2 3: 94 percent / PCC View Scheme |
10,11-dibromo-undecanoic acid
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 7 steps 1: KOH, PEG 400 / 0.5 h / 150 - 200 °C 2: p-TSA / 12 h / Ambient temperature 3: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 4: 84 percent / O3 / CH2Cl2 / -78 °C 5: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 6: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 7: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 8 steps 1: 97 percent / Br2 / CCl4 / 1.5 h 2: KOH, PEG 400 / 0.5 h / 150 - 200 °C 3: p-TSA / 12 h / Ambient temperature 4: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 5: 84 percent / O3 / CH2Cl2 / -78 °C 6: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 7: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 8: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: p-TSA / 12 h / Ambient temperature 2: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 3: 84 percent / O3 / CH2Cl2 / -78 °C 4: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 5: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 6: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme |
9-undecynoic acid methyl ester
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 96 percent / H2, quinoline / 5percent Pd/BaSO4 / hexane / Ambient temperature 2: 84 percent / O3 / CH2Cl2 / -78 °C 3: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 4: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 5: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme |
(Z)-0-undecenoic acid methyl ester
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 84 percent / O3 / CH2Cl2 / -78 °C 2: 1.) NaNH2 / 1.) THF, RT, 1 h, 2.) THF, from -10 deg C to RT 3: 96 percent / LAH / tetrahydrofuran / 5 h / -10 - 20 °C 4: 84 percent / pyridinium chlorochromate / CH2Cl2 / 1 h / Ambient temperature View Scheme |
2-(8-bromooctyloxy)tetrahydropyran
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 2: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 3: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 4: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme | |
Multi-step reaction with 4 steps 1.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 1.2: 16 h / Reflux 2.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 3.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 4.1: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme |
1,8-Octanediol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 6 steps 1: 75 percent / 48percent HBr / Heating 2: 99 percent / p-toluenesulfonic acid 3: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 4: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 5: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 6: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme |
8-bromooctanol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 99 percent / p-toluenesulfonic acid 2: 1.) LiNH2, HMPTA / 1.) RT, 1 h, 2.) a) 10 deg C, 1 h, b) RT, 15 h, c) 55 deg C, 10 h 3: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 4: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 5: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme | |
Multi-step reaction with 5 steps 1.1: toluene-4-sulfonic acid / dichloromethane / 16.5 h / 0 - 20 °C 2.1: n-butyllithium / hexane; tetrahydrofuran / 1 h / -30 - 0 °C / Inert atmosphere 2.2: 16 h / Reflux 3.1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 4.1: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 5.1: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme |
1-tetrahydropyranyloxy-n-9-hexadecyn
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 85 percent / p-TsOH / methanol; H2O / 18 h / 20 °C 2: 1.) iso-BuMgBr, 2.) Cp2TiCl2 / 1.) diethyl ether, 0 deg C, 15 min, 2.) diethyl ether, RT, 3 h 3: 98 percent / pyridinium chlorochromate / CH2Cl2 / 2 h / 20 °C View Scheme | |
Multi-step reaction with 3 steps 1: potassium hydroxide; palladium diacetate / N,N-dimethyl-formamide / 16 h / 145 °C / Sealed tube 2: toluene-4-sulfonic acid / methanol / 16 h / 20 °C 3: pyridinium chlorochromate / dichloromethane / 16 h / 20 °C View Scheme |
9-acetoxynonal
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1.) sodium bis(trimethylsilyl)amide / 1.) THF, from 50 to 55 deg C, 60 min, 2.) THF, a) -78 deg C, 30 min, b) 20 deg C, 12 h 2: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 3: 67 percent / pyridinium chlorochromate / CH2Cl2 / 0.67 h / 20 °C View Scheme |
(Z)-hexadec-9-en-1-yl acetate
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 82 percent / LiAlH4 / diethyl ether / 5 h / 20 °C 2: 67 percent / pyridinium chlorochromate / CH2Cl2 / 0.67 h / 20 °C View Scheme |
2-dec-9-ynyloxy-tetrahydro-pyran
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: LiNH2 / liquid ammonia 2: p-TsOH / methanol 3: 86 percent / H2 / P2Ni 4: 70 percent / PCC View Scheme |
9-tetradecyn-1-ol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 86 percent / H2 / P2Ni 2: 70 percent / PCC View Scheme |
9-decyn-1-ol
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
Multi-step reaction with 5 steps 1: 85 percent / p-TsOH / CH2Cl2 / Ambient temperature 2: LiNH2 / liquid ammonia 3: p-TsOH / methanol 4: 86 percent / H2 / P2Ni 5: 70 percent / PCC View Scheme |
(Z)-9-hexadecenal
cis-9-hexadecenoic acid
Conditions | Yield |
---|---|
With sodium chlorite; sodium dihydrogenphosphate; 2-methyl-but-2-ene In tetrahydrofuran; water; tert-butyl alcohol at 20℃; | 95% |
(Z)-9-hexadecenal
methyl (triphenylphosphoranylidene)acetate
Conditions | Yield |
---|---|
In dichloromethane at 20℃; | 90% |
(Z)-9-hexadecenal
Conditions | Yield |
---|---|
With methyl (triphenylphosphoranylidene)acetate In dichloromethane at 20℃; | 90% |
Conditions | Yield |
---|---|
In diethyl ether at 0 - 10℃; |
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