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

HRID 507977노트

반응식

HRID 507977 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.[CH2:12](O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.C(P(CCCC)CCCC)CCC.N(C(N1CCCCC1)=O)=NC(N1CCCCC1)=O>O1CCCC1.CCCCCC>[CH2:12]([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:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

참가 물질

7

반응물 4

HCID 244Benzyl AlcoholHCID 13831TributylphosphineHCID 730421,1'-(Azodicarbonyl)dipiperidineHCID 2331475-Hydroxy-1-indanone

생성물 1

HCID 107524065-(benzyloxy)-2,3-dihydro-1H-inden-1-one수율 78%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8058Hexane용매

실험 절차

A solution of 5-hydroxyindan-1-one (1.00 q, 6.17 mmol), benzyl alcohol (800 mg, 7.40 mmol) and tributylphosphine (1.70 g, 8.40 mmol) in tetrahydrofuran (80 mL) was stirred at room temperature, 1,1′-(azodicarbonyl)dipiperidine (2.12 g, 8.40 mmol) was added, and the mixture was stirred for 24 hr. Hexane was added to the reaction mixture, the precipitated insoluble material was filtered off, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane) to give the title compound (1.14 g, yield 78%) as pale-yellow crystals.

후처리

  1. filtrationthe precipitated insoluble material was filtered off
  2. concentrationthe filtrate was concentrated under reduced pressure
  3. customThe residue was purified by silica gel column chromatography (5%-40% ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-a18fc6fc942a48f6912acfc6b6752020
출처 데이터셋
uspto-grants-2010_08
특허 번호
US07786165B2

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