Ethanol → HCID 178476801, compound

HRID 1612783Notes

Reaction equation

HRID 1612783 reaction equation
C(OC([P:9]([CH:14]=[C:15]([C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[CH:19][CH:18]=1)[CH3:16])(=[O:13])[O:10][CH2:11][CH3:12])(OCC)C)C.C(O)C.C[Si](C)(C)Cl>ClCCl>[Cl:23][C:20]1[CH:19]=[CH:18][C:17]([C:15]([CH3:16])=[CH:14][PH:9](=[O:13])[O:10][CH2:11][CH3:12])=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 6397ChlorotrimethylsilaneHCID 53725362HCID 53725362, compound

Product 1

HCID 178476801HCID 178476801, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 14.42 g of ethyl (1,1-diethoxyethyl)-2-(4-chlorophenyl)prop-1-enylphosphinate in 50 ml of anhydrous dichloromethane containing 10% of absolute ethanol is treated with 6.518 g of trimethylchlorosilane. After stirring at room temperature for 24 hours the volatile material is removed under reduced pressure. Chromatography of the resulting oil on silica-gel gives ethyl 2-(4-chlorophenyl)prop-1-enylphosphinate as a colourless oil; 1H-NMR (CDCl3): δ(ppm)=7.35 (4H, m, Ph), 7.05 (1H, d, t, J=549 and 1.5 Hz, P--H), 5.56 (1H, d, CH), 5.30 (1H, d, CH), 4.20-3.97 (2H, q, CH2OP), 3.07 (2H, d, t, J=17+1.5 Hz, P--CH2), 1.27 (3H, t, CH3).

Workup

  1. customis removed under reduced pressure

Sources & evidence

ORD record
ord-8c1f850754a94038834c92f692f0c838
Source dataset
uspto-grants-1993_03
Patent number
US05190934

Reaction notes

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