Diphenylphosphinic chloride → Diphenyl-phosphinic acid 4-cyclohexyl-benzyl ester

HRID 237882Notes

Reaction equation

HRID 237882 reaction equation
[CH:1]1([C:7]2[CH:14]=[CH:13][C:10]([CH2:11][OH:12])=[CH:9][CH:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[C:15]1([P:21](Cl)([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[O:22])[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>ClCCl.C(N(CC)CC)C.CN(C1C=CC=CN=1)C>[CH:1]1([C:7]2[CH:8]=[CH:9][C:10]([CH2:11][O:12][P:21]([C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=3)([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:22])=[CH:13][CH:14]=2)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

6

Reactant 2

HCID 73910Diphenylphosphinic chlorideHCID 22492024(4-Cyclohexylphenyl)methanol

Product 1

HCID 68529340Diphenyl-phosphinic acid 4-cyclohexyl-benzyl esterYield 93.5%

Reagents, catalysts & solvents 3

HCID 218852-DimethylaminopyridineCatalystHCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

To a stirred solution of 4-cyclohexylbenzyl alcohol (1 g, 5.26 mmol) in 45 ml of dry dichloromethane, 5 ml of triethylamine and 41 mg of dimethylaminopyridine was added 1.05 ml (1.25 g) of diphenylphosphinic chloride. The mixture was stirred at room temperature for 3 h after which it was concentrated to approximately 10 ml. The mixture was diluted with dichloromethane, washed with cold 10% sodium bicarbonate, water, dried (sodium sulfate), filtered and concentrated to approximately 10 ml. The resulting solution was chromatographed on silica gel, eluting with ethyl acetate/heptane to provide 1.92 g of the title compound.

Workup

  1. concentrationwas concentrated to approximately 10 ml
  2. additionThe mixture was diluted with dichloromethane
  3. washwashed with cold 10% sodium bicarbonate, water
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated to approximately 10 ml
  7. customThe resulting solution was chromatographed on silica gel
  8. washeluting with ethyl acetate/heptane

Sources & evidence

ORD record
ord-c08e86facca243f7a8cb64051ba5db22
Source dataset
uspto-grants-2014_02
Patent number
US08642603B2

Reaction notes

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