(E)-pent-1-en-1-yl-1,3,2-benzodioxaborole
(Z)-11-hydroxy-1-undecenyl bromide
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
With tetrakis(triphenylphosphine) palladium(0); sodium ethanolate In ethanol; benzene for 2.5h; Heating; | 77% |
ω-(Ethoxycarbonyl)nonanal
<(E)-hex-2-enyl>triphenylphosphonium bromide
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
(i) NaOEt, EtOH, (ii) LiAlH4; Multistep reaction; |
ω-(Ethoxycarbonyl)nonanal
<(E)-hex-2-enyl>triphenylphosphonium bromide
A
(10Z,12E)-hexadecadien-1-ol
B
(10E,12E)-hexadeca-10,12-dien-1-ol
Conditions | Yield |
---|---|
(i) NaOEt, EtOH, (ii) LiAlH4; Multistep reaction; |
Conditions | Yield |
---|---|
With quinoline; hydrogen; Lindlar's catalyst |
Conditions | Yield |
---|---|
With lithium aluminium tetrahydride In diethyl ether |
1-Pentyne
(Z)-11-hydroxy-1-undecenyl bromide
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
With benzo[1,3,2]dioxaborole; tetrakis(triphenylphosphine) palladium(0) Yield given. Multistep reaction; |
(E)-(11-hydroxy-1-undecenyl)boronic acid
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: 1.) Br2; 2.) NaOEt / 1.) CHCl3, CCl4, -10 to 0 deg C, 1 h; 2.) CHCl3, CCl4, ethanol, 30 min 2: 77 percent / Pd(PPh3)4/NaOEt / benzene; ethanol / 2.5 h / Heating View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: 1) 1,3,2-benzodioxaborole, then hydrolysis; 2) bromine 2: NaOMe 3: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 3 steps 1: Br2 / -10 - 0 °C 2: NaOMe 3: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 4 steps 1: LiAlH4 2: Br2 / -10 - 0 °C 3: NaOMe 4: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme |
10,11-Dibromo-1-undecanol
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: NaOMe 2: 1) 1,3,2-benzodioxaborole / 2) Pd(PPh3)4 View Scheme |
2-(9-bromononyloxy)tetrahydropyran
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) NaNH2, liq. NH3, (ii) aq. H2SO4, MeOH 2: H2, quinoline / Lindlar catalyst View Scheme |
(E)-1-bromo-2-hexene
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme | |
Multi-step reaction with 2 steps 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) O3, CH2Cl2, (ii) (reduction) 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme | |
Multi-step reaction with 2 steps 1: (i) O3, CH2Cl2, (ii) (reduction) 2: (i) NaOEt, EtOH, (ii) LiAlH4 View Scheme |
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: (i) NaNH2, liq. NH3, (ii) aq. H2SO4, MeOH 2: H2, quinoline / Lindlar catalyst View Scheme |
Hexadeca-10c,12t-dien-1-saeure
(10Z,12E)-hexadecadien-1-ol
Conditions | Yield |
---|---|
Multi-step reaction with 2 steps 1: diethyl ether 2: LiAlH4 / diethyl ether View Scheme |
(10Z,12E)-hexadecadien-1-ol
4-(4-nitrophenylazo)benzoyl chloride
Hexadecadien-(10c,12t)-yl-(1)-4'-nitro-azobenzol-carbonsaeure-(4)-ester
Conditions | Yield |
---|---|
With pyridine |
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