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

HRID 237882

반응식

HRID 237882 반응식
[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

참가 물질

6

반응물 2

HCID 73910Diphenylphosphinic chlorideHCID 22492024(4-Cyclohexylphenyl)methanol

생성물 1

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

시약·촉매·용매 3

HCID 218852-Dimethylaminopyridine촉매HCID 6344Dichloromethane용매HCID 8471Triethylamine용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-c08e86facca243f7a8cb64051ba5db22
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642603B2

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