Water → 5-(benzyloxy)-2,3-dihydro-1H-inden-1-one

HRID 278437ノート

反応式

HRID 278437 の反応式
[OH: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.C([O-])([O-])=O.[K+].[K+].[CH2:18](Br)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.O>CN(C=O)C.CCOC(C)=O>[CH2:18]([O: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)[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

参加物

7

反応物 4

HCID 962WaterHCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 2331475-Hydroxy-1-indanone

生成物 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-one収率 70.5%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

A mixture of 5-hydroxy-indan-1-one (5.3 g, 35.7 mmol), KJ (0.6 g, 3.6 mmol) and K2CO3 (6.17 g, 44.6 mmol) and benzyl bromide (4.66 ml, 39.3 mmol) in DMF (50 ml) were heated at 100° C. for 1 hr. Addition of H2O (150 ml) and extraction with EtOAc (3×50 ml), washing the organic phase with satd. NaCl solution (100 ml) and drying with MgSO4 and evaporation afforded a brown solid. This material was recrystallised twice from EtOH to afford 5-benzyloxy-indan-1-one (6 g, 25.17 mmol, 70%) as yellow crystals, Mp. 105-106° C., MS m/e=238.1 (M+).

後処理

  1. washwashing the organic phase with satd
  2. dry with materialNaCl solution (100 ml) and drying with MgSO4 and evaporation
  3. customafforded a brown solid
  4. customThis material was recrystallised twice from EtOH

出典と根拠

ORDレコード
ord-99c56832d9ff4460af9ad6568e2c193c
出典データセット
uspto-grants-2002_03
特許番号
US06359138B1

反応ノート

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