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

HRID 1722641ノート

反応式

HRID 1722641 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8058Hexane溶媒

反応条件

温度
0 °C

実験手順

To 17.6 ml n-butyllithium (2.5 M, 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.

後処理

  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

出典と根拠

ORDレコード
ord-4896b919fb614b5eb3c8ba0264a88373
出典データセット
uspto-grants-1989_08
特許番号
US04857517

反応ノート

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