Sodium Hydroxide → tert-Butyl (triphenylphosphoranylidene) acetate

HRID 2106871Notes

Reaction equation

HRID 2106871 reaction equation
[Br-].[C:2]([CH2:9][P+:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3].[OH-].[Na+]>O>[C:2]([CH:9]=[P:10]([C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1)([C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)([O:4][C:5]([CH3:8])([CH3:7])[CH3:6])=[O:3]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 2733853(tert-Butoxycarbonylmethyl)triphenylphosphonium Bromide

Product 1

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateYield 95.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A suspension of the carbo-t-butoxymethyl triphenylphosphonium bromide (55.8 g, 122 mmol) in water (400 ml) was treated with sodium hydroxide (4.7 g, 117 mml) in water (100 ml). The mixture was stirred for 16 hours and the solid collected to give 43.7 g (95% of theory) of carbo-t-butoxymethylene triphenylphosphorane.

Workup

  1. customthe solid collected

Sources & evidence

ORD record
ord-cd2b28a359094e00a1ef858780e8214b
Source dataset
uspto-grants-1990_06
Patent number
US04931469

Reaction notes

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