Triethylsilane → Ethyl 4-([1,1'-biphenyl]-4-yl)butanoate

HRID 2352572노트

반응식

HRID 2352572 반응식
C([SiH](CC)CC)C.[C:8]1([C:14]2[CH:28]=[CH:27][C:17]([C:18]([CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=O)=[CH:16][CH:15]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>FC(F)(F)C(O)=O.O>[C:8]1([C:14]2[CH:28]=[CH:27][C:17]([CH2:18][CH2:20][CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])=[CH:16][CH:15]=2)[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

참가 물질

5

반응물 2

HCID 12052TriethylsilaneHCID 12600094Ethyl 4-oxo-4-(4-phenylphenyl)butanoate

생성물 1

HCID 19843451Ethyl 4-([1,1'-biphenyl]-4-yl)butanoate수율 89%

시약·촉매·용매 2

HCID 962Water용매HCID 6422Trifluoroacetic acid용매

실험 절차

Triethylsilane (32.62 ml) was added in one portion to a stirred solution of ethyl 3-(4-phenylbenzoyl)propanoate [(2), 25.06 g] in trifluoroacetic acid (71.5 ml) and the resulting mixture was stirred at room temperature for about 20 hours. The resulting clear dark orange solution was diluted with water and extracted with ether. The extracts were washed with aqueous sodium bicarbonate (x2) and then water (x2), dried and concentrated to give a mobile brown liquid. Triethylsilane remaining in this liquid was removed by Kugelrohr evaporative distillation at 110° C. and a pressure of ca. 1 mmHg to leave crude ethyl 4-(4-phenylphenyl)butanoate (21.20 g) as a brown oil. (Compare method of C. T. West, S. J. Donnelly, D. A. Kooistra and M. P. Doyle, J. Org. Chem., 1973, 38, 2675).

후처리

  1. extractionextracted with ether
  2. washThe extracts were washed with aqueous sodium bicarbonate (x2)
  3. dry with materialwater (x2), dried
  4. concentrationconcentrated
  5. customto give a mobile brown liquid
  6. customTriethylsilane remaining in this liquid was removed by Kugelrohr evaporative distillation at 110° C.

출처 및 근거

ORD 기록
ord-9ee1429c92e7409bbc4d2a2d32de4ee8
출처 데이터셋
uspto-grants-1989_10
특허 번호
US04877811

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