Carbon Dioxide → 2,3,4,5-Tetrahydro-1-benzoxepin-9-carboxylic acid

HRID 1650366노트

반응식

HRID 1650366 반응식
C([Li])CCC.CN(C)CCN(C)C.[O:14]1[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][CH2:16][CH2:15]1.[C:25](=[O:27])=[O:26]>CCCCCC.O>[O:14]1[C:20]2[C:21]([C:25]([OH:27])=[O:26])=[CH:22][CH:23]=[CH:24][C:19]=2[CH2:18][CH2:17][CH2:16][CH2:15]1

참가 물질

7

반응물 4

HCID 280Carbon DioxideHCID 8037N,N,N',N'-TetramethylethylenediamineHCID 225522,3,4,5-Tetrahydro-1-benzoxepineHCID 178418339Butyllithium

생성물 1

HCID 127011502,3,4,5-Tetrahydro-1-benzoxepin-9-carboxylic acid

시약·촉매·용매 2

HCID 962Water용매HCID 8058Hexane용매

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온도
0 °C

실험 절차

To 17.6 ml n-butyllithium (2.5M, 0.044 mol) in 63 ml hexane is added dropwise (0.044 mol) 5.1 g tetramethylethylenediamine (TMEDA) and 5 g (0.034 mol) of 2,3,4,5-tetrahydro-1-benzoxepin. The reaction mixture is stirred overnight. The reaction mixture is then chilled to 0° C. and carbonated with dry ice for an hour. Water (110 ml) is added and the mixture is filtered and the aqueous phase acidified with 4N HCl. The resultant oil is extracted into methylene chloride and dried (MgSO4). After filtering and concentrating in vacuo, 2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid results as a tan solid.

후처리

  1. filtrationthe mixture is filtered
  2. extractionThe resultant oil is extracted into methylene chloride
  3. dry with materialdried (MgSO4)
  4. filtrationAfter filtering
  5. concentrationconcentrating in vacuo, 2,3,4,5-tetrahydro-1-benzoxepin-9-carboxylic acid
  6. customresults as a tan solid

출처 및 근거

ORD 기록
ord-51ebac0614dc4feda53ff77b2eede7b5
출처 데이터셋
uspto-grants-1990_05
특허 번호
US04924010

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