Hydrochloric Acid → 5-Chloro-2,3-dihydro-1H-inden-1-ol

HRID 582925ノート

反応式

HRID 582925 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[C:7](=[O:11])[CH2:6][CH2:5]2.[OH-].[Na+].[BH4-].[Na+].Cl>O.C1COCC1>[OH:11][CH:7]1[C:8]2[C:4](=[CH:3][C:2]([Cl:1])=[CH:10][CH:9]=2)[CH2:5][CH2:6]1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 1425995-Chloro-1-indanoneHCID 4311764Sodium borohydride

生成物 1

HCID 225048045-Chloro-2,3-dihydro-1H-inden-1-ol収率 83%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
2.5 °C

実験手順

A mixture of 2.5 g of 5-chloroindan-1-one and 30 ml of THF is cooled to 0-5° C., 2.5 ml of concentrated NaOH solution and then, in portions, 0.88 g of sodium borohydride are added and the reaction mixture is stirred overnight at RT. It is poured into 100 ml of water, the mixture is acidified to pH 2 by the addition of concentrated HCl solution, extracted with AcOEt, the organic phase is washed with saturated NaCl solution and dried over Na2SO4 and the solvent is evaporated off under vacuum. The residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v) to give 2.1 g of the expected product.

後処理

  1. extractionextracted with AcOEt
  2. washthe organic phase is washed with saturated NaCl solution
  3. dry with materialdried over Na2SO4
  4. customthe solvent is evaporated off under vacuum
  5. customThe residue is chromatographed on silica using a cyclohexane/AcOEt mixture (80/20; v/v)

出典と根拠

ORDレコード
ord-3c979d0db6d44c47a6d47fc5f9d8de67
出典データセット
uspto-grants-1999_07
特許番号
US05925768

反応ノート

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