Water → HCID 13663047、化合物

HRID 280623ノート

反応式

HRID 280623 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([C:11](Cl)=[O:12])[S:7][C:6]=2[CH:14]=1.[H-].[Al+3].[Li+].[H-].[H-].[H-].O.[OH-].[Na+]>CCOCC.O1CCCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([CH2:11][OH:12])[S:7][C:6]=2[CH:14]=1

参加物

7

反応物 4

HCID 962Water2 回HCID 14798Sodium HydroxideHCID 34579746-Bromo-3-chloro-1-benzothiophene-2-carbonyl chlorideHCID 21226445Aluminium lithium hydride2 回

生成物 1

HCID 13663047HCID 13663047、化合物収率 40%

試薬・触媒・溶媒 2

HCID 3283Diethyl Ether溶媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 6-bromo-3-chlorobenzo[b]thiophene-2-carboxylic acid chloride (6.20 g) in dry ether (50 ml) and dry tetrahydrofuran (50 ml) was added dropwise to a stirred suspension of lithium aluminium hydride (0.58 g) in dry ether (250 ml) at 0° under an atmosphere of dry nitrogen. The mixture was stirred at room temperature for 30 minutes and then at reflux for 21/2 hours before being cooled and allowed to stand for 18 hours. It was then cooled and the excess of lithium aluminium hydride was decomposed by the cautious addition of water (1.0 ml) followed by 5N sodium hydroxide (1.0 ml) followed by water (2.0 ml) with vigorous stirring. The mixture was filtered and the filtrate was evaporated to give a solid which was chromatographed on silica gel. Elution with chloroform first gave some impurity followed by pure product. The product containing fractions were combined and evaporated to give a solid which was crystallised from chloroform to give 6-bromo-3-chloro-2-hydroxymethylbenzo[ b]thiophene (2.22 g), m.p. 117°-118°.

後処理

  1. temperatureat reflux for 21/2 hours
  2. temperaturebefore being cooled
  3. waitto stand for 18 hours
  4. temperatureIt was then cooled
  5. filtrationThe mixture was filtered
  6. customthe filtrate was evaporated
  7. customto give a solid which
  8. customwas chromatographed on silica gel
  9. washElution with chloroform
  10. customfirst gave some impurity
  11. additionThe product containing fractions
  12. customevaporated
  13. customto give a solid which
  14. customwas crystallised from chloroform

出典と根拠

ORDレコード
ord-2215253d5e9d4aca8d62f81213b2a120
出典データセット
uspto-grants-1986_05
特許番号
US04590200

反応ノート

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