Water → HCID 178454801, compound

HRID 1292574Notes

Reaction equation

HRID 1292574 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([P-:7][C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.[K+].F[C:16]1[CH:21]=[CH:20][C:19]([CH2:22][PH:23](=[O:29])[O:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=1.O>C1COCC1>[C:8]1([P:7]([C:4]2[CH:3]=[CH:2][CH:1]=[CH:6][CH:5]=2)[C:16]2[CH:21]=[CH:20][C:19]([CH2:22][PH:23](=[O:29])[O:24][CH2:25][CH:26]([CH3:28])[CH3:27])=[CH:18][CH:17]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 962WaterHCID 11042360KPPh2HCID 178454800HCID 178454800, compound

Product 1

HCID 178454801HCID 178454801, compoundYield 98.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
23 °C

Procedure

200 ml (100 mmol) of potassium diphenylphosphide solution in THF (manufacturer: Aldrich) were added dropwise at -5° C. to a solution of 21.90 g (95 mmol) of isobutyl 4-fluorophenylmethylphosphinate in 150 ml of THF. After stirring for 20 hours at 23° C., the mixture was hydrolyzed by addition of 250 ml of degassed water and stirring for 15 minutes. Extraction with ethyl acetate, drying of the organic phase over Na2SO4, evaporation on a rotary evaporator and drying under reduced pressure gave 37.0 g of isobutyl (4-diphenylphosphinophenyl)methylphosphinate in the form of a yellow oil.

Workup

  1. stirringstirring for 15 minutes
  2. extractionExtraction with ethyl acetate
  3. dry with materialdrying of the organic phase over Na2SO4, evaporation on a rotary evaporator
  4. customdrying under reduced pressure

Sources & evidence

ORD record
ord-9d471c0e270d40a5b0d8ed716dbc9061
Source dataset
uspto-grants-1998_05
Patent number
US05756804

Reaction notes

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