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

HRID 445852

Reaction equation

HRID 445852 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-2b9a860869ac44618919f38e159b26dd
Source dataset
uspto-grants-2013_07
Patent number
US08476308B2

Linked notes

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