CAS No.56039-93-1,Magnesium, 3-butenylchloro- Suppliers

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Synthetic route

: (E)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 4-(tert-butyldimethylsilyl)-2-((4-methoxyphenyl)imino)but-3-ynoate

: 56039-93-1
3-butenylmagnesium chloride

: (R)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 2-((tert-butyldimethylsilyl)ethynyl)-2-(phenylamino)hex-5-enoate

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran at 20℃; for 1h; Schlenk technique; Stage #2: (E)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 4-(tert-butyldimethylsilyl)-2-((4-methoxyphenyl)imino)but-3-ynoate In tetrahydrofuran at -78℃; for 0.0833333h; Schlenk technique; diastereoselective reaction;	94%

Yield

Stage #1: 3-butenylmagnesium chloride With (trimethylsilyl)methylmagnesium chloride; lithium chloride; zinc(II) chloride In tetrahydrofuran at 20℃; for 1h; Schlenk technique;
Stage #2: (E)-(1R,2S,5R)-5-methyl-2-(2-phenylpropan-2-yl)cyclohexyl 4-(tert-butyldimethylsilyl)-2-((4-methoxyphenyl)imino)but-3-ynoate In tetrahydrofuran at -78℃; for 0.0833333h; Schlenk technique; diastereoselective reaction;

94%

: potassium iodomethyltrifluoroborate

: 56039-93-1
3-butenylmagnesium chloride

: potassium 1-propenyltrifluoroborate

Conditions

Conditions	Yield
In tetrahydrofuran at -25 - 0℃;	85%

: 56039-93-1
3-butenylmagnesium chloride

: 78-84-2
isobutyraldehyde

: 2,9-dimethyl-dec-5-ene-3,8-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: isobutyraldehyde In diethyl ether at -50 - -30℃; for 1h; Further stages.;	85%

: 56039-93-1
3-butenylmagnesium chloride

: 500548-54-9
tert-butyl (2S)-5-bromo-2-(methoxyacetyl)indoline-1-carboxylate

A: (S)-5-Bromo-2-((S)-1-hydroxy-1-methoxymethyl-pent-4-enyl)-2,3-dihydro-indole-1-carboxylic acid tert-butyl ester

B: 849479-96-5
tert-butyl (2S)-5-bromo-2-[(1R)-1-hydroxy-1-(methoxymethyl)-pent-4-enyl]-indoline-1-carboxylate

Conditions

Conditions	Yield
In tetrahydrofuran at -78℃; for 0.25h; Grignard addition;	A n/a B 82%

...Expand

: 110-62-3
pentanal

: 56039-93-1
3-butenylmagnesium chloride

: tetradec-7-ene-5,10-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: pentanal In diethyl ether at -50 - -30℃; Further stages.;	82%

: 74372-90-0
3,4,6-tri-O-benzyl-D-glucal epoxide

: 56039-93-1
3-butenylmagnesium chloride

: (3S,4R,5R,6R)-4,5-Bis-benzyloxy-6-benzyloxymethyl-2-but-3-enyl-tetrahydro-pyran-3-ol

Conditions

Conditions	Yield
at -60 - 0℃;	80%

: chloro(cyclopentadienyl)(triphenylphosphine)nickel(II)

: 56039-93-1
3-butenylmagnesium chloride

: C5H5Ni(P(C6H5)3)CH2CH2CHCH2

Conditions

Conditions	Yield
In diethyl ether; water; benzene C5H5Ni(P(C6H5)3)Cl in C6H6; added to a cooled soln. of CH2CH2CHCH2MgCl in ether; hydrolysis with aq. soln. of NH4Cl; purifn. of org. phase by chromy. on Al2O3; eluted with C6H6/hexane; crystd. by cooling and addn. of n-hexane;	80%
In diethyl ether; water; benzene C5H5Ni(P(C6H5)3)Cl in C6H6; added to a cooled soln. of CH2CH2CHCH2MgCl in ether; hydrolysis with aq. soln. of NH4Cl; purifn. of org. phase by chromy. on Al2O3; eluted with C6H6/hexane; crystd. by cooling and addn. of n-hexane;	80%

: 78-82-0
Isobutyronitrile

: 56039-93-1
3-butenylmagnesium chloride

: 77958-21-5
2-methyl-hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: Isobutyronitrile In diethyl ether at -50 - -30℃; for 1h; Further stages.;	79%

: 108-94-1
cyclohexanone

: 56039-93-1
3-butenylmagnesium chloride

: 1-[4-(1-hydroxy-cyclohexyl)-but-2-enyl]-cyclohexanol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: cyclohexanone In diethyl ether at -50 - -30℃; Further stages.;	78%

: 56039-93-1
3-butenylmagnesium chloride

: 120-92-3
cyclopentanone

: 1-[4-(1-hydroxy-cyclopentyl)-but-2-enyl]-cyclopentanol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: cyclopentanone In diethyl ether at -50 - -30℃; Further stages.;	78%

: 56039-93-1
3-butenylmagnesium chloride

: 120-92-3
cyclopentanone

: 107-12-0
propiononitrile

: 7-(1-hydroxy-cyclopentyl)-hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Stage #3: cyclopentanone In diethyl ether at -30 - -10℃; for 1h; Further stages.;	76%

...Expand

: 56039-93-1
3-butenylmagnesium chloride

: 107-12-0
propiononitrile

: 63407-93-2
hept-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Further stages.;	76%

: 38312-94-6
4,4-dimethyl-1-cyclopentene-1-carboxaldehyde

: 56039-93-1
3-butenylmagnesium chloride

: 1-(4,4-dimethylcyclopent-1-en-1-yl)pent-4-en-1-ol

Conditions

Conditions	Yield
In tetrahydrofuran at 0℃; for 0.666667h; Inert atmosphere;	75%

: 160661-42-7
(R)-(–)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-dimethylhept-5-enal

: 56039-93-1
3-butenylmagnesium chloride

: 106-96-7
propargyl bromide

: (2R)-2-methyl-2-(4-methylpent-3-en-1-yl)dec-9-en-4-yne-1,3-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride; propargyl bromide In tetrahydrofuran at 0 - 20℃; for 5h; Inert atmosphere; Stage #2: (R)-(–)-2-(((tert-butyldimethylsilyl)oxy)methyl)-2,6-dimethylhept-5-enal In tetrahydrofuran at 0 - 20℃; for 1h; Inert atmosphere; Stage #3: With tetrabutyl ammonium fluoride In tetrahydrofuran at 20℃; for 1h; Inert atmosphere;	75%

...Expand

: 1035570-51-4
2-(methoxymethyl)-6-methylaniline

: 56039-93-1
3-butenylmagnesium chloride

: 1035570-56-9
2-(but-3-en-1-yl)-6-methylaniline

Conditions

Conditions	Yield
In tetrahydrofuran at 0 - 25℃; for 12h; Inert atmosphere;	75%

: 833452-10-1
2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-N-methoxy-N-methyl-benzamide

: 56039-93-1
3-butenylmagnesium chloride

: 1-[2-(4-ethyl-2-fluoro-phenylamino)-3,4-difluoro-phenyl]-pent-4-en-1-one

Conditions

Conditions	Yield
In tetrahydrofuran at 20℃; for 0.5h;	70%

: C14H22N2O2

: 56039-93-1
3-butenylmagnesium chloride

: 8-methyl-6-(phenylamino)non-1-en-5-one

Conditions

Conditions	Yield
With sodium carbonate In tetrahydrofuran at -20℃;	68%

: 110-93-0
6-Methyl-hept-5-en-2-on

: 56039-93-1
3-butenylmagnesium chloride

: 2,6,11,15-tetramethyl-hexadeca-2,8,14-triene-6,11-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: 6-Methyl-hept-5-en-2-on In diethyl ether at -50 - -30℃; Further stages.;	67%

: 56039-93-1
3-butenylmagnesium chloride

: 67-64-1
acetone

: 2,7-dimethyl-oct-4-ene-2,7-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: acetone In diethyl ether at -50 - -30℃; Further stages.;	63%

: 123-38-6
propionaldehyde

: 56039-93-1
3-butenylmagnesium chloride

: 107-12-0
propiononitrile

: 8-hydroxy-dec-5-en-3-one

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Stage #3: propionaldehyde In diethyl ether at -30 - -10℃; for 1h; Further stages.;	60%

...Expand

: 107-86-8
3,3-dimethyl acrylaldehyde

: 56039-93-1
3-butenylmagnesium chloride

: 2,11-dimethyl-dodeca-2,6,10-triene-4,9-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: 3,3-dimethyl acrylaldehyde In diethyl ether at -50 - -30℃; Further stages.;	57%

: 78-94-4
methyl vinyl ketone

: 56039-93-1
3-butenylmagnesium chloride

: 3,8-dimethyl-deca-1,5,9-triene-3,8-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: methyl vinyl ketone In diethyl ether at -50 - -30℃; Further stages.;	54%

: 78-94-4
methyl vinyl ketone

: 56039-93-1
3-butenylmagnesium chloride

: 107-12-0
propiononitrile

: 8-hydroxy-8-methyl-deca-5,9-dien-3-one

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - -30℃; for 1h; Stage #3: methyl vinyl ketone In diethyl ether at -30 - -10℃; for 1h; Further stages.;	53%

...Expand

: 858523-33-8
C18H16ClN5O

: 56039-93-1
3-butenylmagnesium chloride

: C22H23N5O

Conditions

Conditions	Yield
With 1-methyl-pyrrolidin-2-one; iron(III) acetylacetonate In tetrahydrofuran at 20℃; for 3h;	48%

: 16196-15-9
(1R,4R)-(+)-bicyclo<2.2.2>oct-5-en-2-one

: 56039-93-1
3-butenylmagnesium chloride

A: C12H18O

B: C12H18O

Conditions

Conditions	Yield
In tetrahydrofuran at -78 - 20℃; for 12h; diastereoselective reaction;	A 45% B 15%

...Expand

: 56039-93-1
3-butenylmagnesium chloride

: 107-12-0
propiononitrile

: dec-5-ene-3,8-dione

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: propiononitrile In diethyl ether at -50 - 35℃; for 4h; Further stages.;	33%

: 110-13-4
2,5-hexanedione

: 56039-93-1
3-butenylmagnesium chloride

: (1S*,2S*,4R*)-1,4-dimethyl-2-vinyl-cyclohexane-1,4-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: 2,5-hexanedione In diethyl ether at -50 - -30℃; Further stages.;	30%

: 56039-93-1
3-butenylmagnesium chloride

: 98-86-2
acetophenone

: (Z)-2,7-Diphenyl-oct-4-ene-2,7-diol

Conditions

Conditions	Yield
Stage #1: 3-butenylmagnesium chloride With titanium(IV) isopropylate In diethyl ether at -70 - -50℃; Stage #2: acetophenone In diethyl ether at -50 - -30℃; Further stages.;	30%

: 833451-95-9
2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-methoxy-N-methyl-benzamide

: 56039-93-1
3-butenylmagnesium chloride

: 1-(2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-phenyl)-pent-4-en-1-one

Conditions

Conditions	Yield
Stage #1: 2-(4-ethynyl-2-fluoro-phenylamino)-3,4-difluoro-N-methoxy-N-methyl-benzamide; 3-butenylmagnesium chloride In tetrahydrofuran at -78℃; for 0.5h; Stage #2: With ammonium chloride In tetrahydrofuran at 20℃;	27%

: (4,4-dimethyl-4-silacyclopent-1-en-1-yl)methanol

: 56039-93-1
3-butenylmagnesium chloride

: 1-(4,4-dimethyl-4-silacyclopent-1-en-1-yl)pent-4-en-1-ol

Conditions

Conditions	Yield
Stage #1: (4,4-dimethyl-4-silacyclopent-1-en-1-yl)methanol With aluminum tri-sec-butoxide; acetic acid In tert-butyl methyl ether at 0℃; for 0.166667h; Inert atmosphere; Stage #2: With 4-nitrobenzaldehdye In tert-butyl methyl ether at 20℃; for 2h; Inert atmosphere; Stage #3: 3-butenylmagnesium chloride In tetrahydrofuran at 0℃; for 1h; Inert atmosphere;	21%

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Synthetic route

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