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 2389899ノート

反応式

HRID 2389899 の反応式
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

参加物

5

反応物 1

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 9893474Tetrabutylammonium Difluorotriphenylsilicate触媒HCID 80711,2-Dimethoxyethane溶媒2 回HCID 25517Ammonium Chloride溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-feafff4fb6af4b6d836378bd911684a0
出典データセット
uspto-grants-2012_09
特許番号
US08273761B2

反応ノート

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