Triphenylphosphine → Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)

HRID 1909567Notes

Reaction equation

HRID 1909567 reaction equation
[CH2:1]([O:3][C:4](=[O:10])[CH:5]([Cl:9])[O:6][CH2:7][CH3:8])[CH3:2].[C:11]1([P:17]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(Cl)(Cl)Cl>[Cl-:9].[CH2:7]([O:6][CH:5]([P+:17]([C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)[C:11]1[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1)[C:4]([O:3][CH2:1][CH3:2])=[O:10])[CH3:8]

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 2724873Ethyl 2-chloro-2-ethoxyacetate

Product 1

HCID 11327835Phosphonium, (1,2-diethoxy-2-oxoethyl)triphenyl-, chloride (1:1)Yield 82%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 2-chloro-2-ethoxyacetic acid ethyl ester (10 g, 60 mmol) in chloroform (30 mL) was added triphenylphosphine (15.7 g, 60 mmol) and stirred overnight at room temperature. The solvent was removed in vacuo, and diethyl ether was added. The solvent was again removed and dried on high vacuum to give (1,2-diethoxy-2-oxoethyl)triphenylphosphonium chloride (21 g, 82% yield) (679) as a foamy solid.

Workup

  1. customThe solvent was removed in vacuo, and diethyl ether
  2. additionwas added
  3. customThe solvent was again removed
  4. customdried on high vacuum

Sources & evidence

ORD record
ord-ad6cdfcf27364c91be4eed3765d58467
Source dataset
uspto-grants-2013_12
Patent number
US08598374B2

Reaction notes

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