3-[4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propanal → 1,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-ol

HRID 2389899노트

반응식

HRID 2389899 반응식
C[Si](C)(C)[C:3]1[C:8]([CH2:9][CH2:10][CH:11]=[O:12])=[CH:7][N:6]=[C:5]2[O:13][CH2:14][CH2:15][C:4]=12>CCCC[N+](CCCC)(CCCC)CCCC.C1C=CC([Si-](F)(F)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.COCCOC.[Cl-].[NH4+]>[CH2:15]1[C:4]2[C:5](=[N:6][CH:7]=[C:8]3[CH2:9][CH2:10][CH:11]([OH:12])[C:3]3=2)[O:13][CH2:14]1

참가 물질

5

반응물 1

HCID 591794483-[4-(Trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propanal

생성물 1

HCID 591793711,6,7,8-tetrahydro-2H-cyclopenta[d]furo[2,3-b]pyridin-8-ol수율 71%

시약·촉매·용매 3

HCID 9893474Tetrabutylammonium Difluorotriphenylsilicate촉매HCID 80711,2-Dimethoxyethane용매2회HCID 25517Ammonium Chloride용매

실험 절차

To a solution of tetrabutylammonium difluorotriphenylsilicate (43.3 mg, 0.802 mmol) in 1,2-dimethoxyethane (3 mL) heated to 70° C. was added dropwise a solution of 3-[4-(trimethylsilyl)-2,3-dihydrofuro[2,3-b]pyridin-5-yl]propanal (100 mg, 0.401 mmol) in 1,2-dimethoxyethane (1 mL). After dropwise addition, the reaction solution was diluted with saturated aqueous ammonium chloride solution, and the mixture was extracted with ethyl acetate. The extract was washed with saturated brine and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure and the residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0) to give the title compound (50.4 mg, yield 71%).

후처리

  1. additionAfter dropwise addition
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe extract was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane=30/70→100/0)

출처 및 근거

ORD 기록
ord-feafff4fb6af4b6d836378bd911684a0
출처 데이터셋
uspto-grants-2012_09
특허 번호
US08273761B2

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