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

HRID 2352572ノート

反応式

HRID 2352572 の反応式
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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6422Trifluoroacetic acid溶媒

実験手順

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).

後処理

  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.

出典と根拠

ORDレコード
ord-9ee1429c92e7409bbc4d2a2d32de4ee8
出典データセット
uspto-grants-1989_10
特許番号
US04877811

反応ノート

読み込み中…