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 2389899Notes

Reaction equation

HRID 2389899 reaction equation
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

Participants

5

Reactant 1

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 9893474Tetrabutylammonium DifluorotriphenylsilicateCatalystHCID 80711,2-DimethoxyethaneSolvent2×HCID 25517Ammonium ChlorideSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-feafff4fb6af4b6d836378bd911684a0
Source dataset
uspto-grants-2012_09
Patent number
US08273761B2

Reaction notes

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