Tetrahydrofuran → 4-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one

HRID 2171019노트

반응식

HRID 2171019 반응식
[Si](CO[C:20]1([CH2:23][O:24][C:25]2[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[CH:27][C:26]=2[C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][CH2:38][C:39]3=[O:44])[CH2:22][CH2:21]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.O.O.O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[O:66]1CCC[CH2:67]1>>[OH:66][CH2:67][C:20]1([CH2:23][O:24][C:25]2[C:30]([O:31][CH3:32])=[C:29]([O:33][CH3:34])[CH:28]=[CH:27][C:26]=2[C:35]2[CH:43]=[CH:42][CH:41]=[C:40]3[C:36]=2[CH2:37][CH2:38][C:39]3=[O:44])[CH2:22][CH2:21]1

참가 물질

4

반응물 3

HCID 8028TetrahydrofuranHCID 11726816Tetrabutylammonium Fluoride TrihydrateHCID 712796704-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one

생성물 1

HCID 545762924-[2-(1-Hydroxymethyl-cyclopropylmethoxy)-3,4-dimethoxy-phenyl]-indan-1-one

실험 절차

To a stirring solution of 4-(2-((1-((tert-butyldiphenylsilyl)methoxy)cyclopropyl)methoxy)-3,4-dimethoxyphenyl)-2,3-dihydro-1H-inden-1-one (5 g, 6.25 mmol) in tetrahydrofuran, was added tetrabutylammonium fluoride trihydrate (33 mL, 33 mmol) and the resultant reaction mixture was stirred at RT for 16 h. The reaction mixture was quenched with water and extracted with ethyl acetate (3×). The combined ethyl acetate layer was washed with brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. Purification was done by column chromatography (silica gel, 0-40% ethyl acetate in pet ether) to afford the title compound as a yellow solid.

후처리

  1. customthe resultant reaction mixture
  2. customThe reaction mixture was quenched with water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined ethyl acetate layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customPurification

출처 및 근거

ORD 기록
ord-594a496276cc4c2a982159f607125e6e
출처 데이터셋
uspto-grants-2015_06
특허 번호
US09051290B2

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