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

HRID 278437노트

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HRID 278437 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

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+).

후처리

  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

출처 및 근거

ORD 기록
ord-99c56832d9ff4460af9ad6568e2c193c
출처 데이터셋
uspto-grants-2002_03
특허 번호
US06359138B1

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