P-Chloroacetophenone → HCID 360612, compound

HRID 1590384Notes

Reaction equation

C([N-]C1CCCCC1)(C)C.[Li+].C([Li])CCC.C(NC1CCCCC1)(C)C.[CH2:27]([O:29][C:30](=[O:36])[CH2:31][Si](C)(C)C)[CH3:28].[CH3:37][C:38]([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)=O>>[CH2:27]([O:29][C:30](=[O:36])[CH:31]=[C:38]([C:40]1[CH:45]=[CH:44][C:43]([Cl:46])=[CH:42][CH:41]=1)[CH3:37])[CH3:28]

Participants

Reactant 5

HCID 7467P-Chloroacetophenone

HCID 62386Cyclohexylisopropylamine

HCID 77687Ethyl trimethylsilylacetate

HCID 10877271Lithium cyclohexylisopropylamide

HCID 178418339Butyllithium

Product 1

HCID 360612HCID 360612, compound

Procedure

To a solution of lithium isopropylcyclohexylamide (prepared from 12.5 ml of n-butyllithium 1.6M solution and isopropyl cyclohexylamine (3.3 ml) (ex Aldrich) in TMF was added at -60°, ethyltrimethylsilylacetate (3.6 ml) (ex Fluka). After 30 minutes at -60°, 4-chloro acetophenone (ex Aldrich) (1.55 g) was added. After 18 hours at 25° the mixture was partitioned between ether and water and worked up in the usual manner. Purification by chromatography (silica; ether/hexane) gave Ethyl-3-(4-chlorophenyl)-but-2-enoate (1.22 g), as a 1:1 mixture of E:Z olefin isomers. NMR 1H: 7.2(4H,m), 6.0 and 5.0(1H,m), 4.12(2H,m), 2.51 and 1.90(3H,s), 1.25(3H,m).

Workup

additionwas added at -60°
customAfter 18 hours at 25° the mixture was partitioned between ether and water
customPurification by chromatography (silica; ether/hexane)

Sources & evidence

ORD record: ord-71820d7fa5844d8e9ed2957f172cfc19
Source dataset: uspto-grants-1993_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05202356

Reaction notes

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