Carbon Dioxide → 6-Methylbenzo[b]thiophene-3-carboxylic acid

HRID 1583347ノート

反応式

HRID 1583347 の反応式
C([Li])CCC.Br[C:7]1[C:8]2[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][C:9]=2[S:10][CH:11]=1.[C:17](=[O:19])=[O:18]>CCOCC>[CH3:16][C:13]1[CH:14]=[CH:15][C:8]2[C:7]([C:17]([OH:19])=[O:18])=[CH:11][S:10][C:9]=2[CH:12]=1

参加物

5

反応物 3

HCID 280Carbon DioxideHCID 12398618HCID 12398618、化合物HCID 178418339Butyllithium

生成物 1

HCID 136629696-Methylbenzo[b]thiophene-3-carboxylic acid

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

反応条件

温度
-70 °C

実験手順

A solution of n-butyl lithium (15 ml. of 1.0M solution in hexane) was added dropwise to a stirred solution of 3-bromo-6-methylbenzo[b]thiophene (3.0 g.) in dry ether (40 ml.) at -70° C. under an atmosphere of dry nitrogen. The mixture was stirred at -70° C. for 30 minutes and then an excess of crushed solid carbon dioxide was added. When all the carbon dioxide had evaporated, water (25 ml.) was added and the mixture was stirred for a few minutes. The organic layer was separated and washed with 2N.NaOH solution. The aqueous layer and NaOH extract were combined and acidified with concentrated hydrochloric acid. The solid was filtered off, washed with water, dried and crystallized from toluene to give 6-methylbenzo[b]thiophene-3-carboxylic acid (1.60 g.), m.p. 205°-209°.

後処理

  1. customWhen all the carbon dioxide had evaporated
  2. additionwater (25 ml.) was added
  3. stirringthe mixture was stirred for a few minutes
  4. customThe organic layer was separated
  5. washwashed with 2N
  6. extractionThe aqueous layer and NaOH extract
  7. filtrationThe solid was filtered off
  8. washwashed with water
  9. customdried
  10. customcrystallized from toluene

出典と根拠

ORDレコード
ord-5812d4a043464c9bb52807ab79049fe1
出典データセット
uspto-grants-1985_11
特許番号
US04551468

反応ノート

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