Diisobutylaluminum hydride → 5-Methyl-2-(trifluoromethyl)-3-furanmethanol

HRID 237252노트

반응식

HRID 237252 반응식
C([O:3][C:4]([C:6]1[CH:10]=[C:9]([CH3:11])[O:8][C:7]=1[C:12]([F:15])([F:14])[F:13])=O)C.CC(C[AlH]CC(C)C)C>CCOCC>[CH3:11][C:9]1[O:8][C:7]([C:12]([F:15])([F:13])[F:14])=[C:6]([CH2:4][OH:3])[CH:10]=1

참가 물질

4

반응물 2

HCID 14487Diisobutylaluminum hydrideHCID 2737208Ethyl 5-methyl-2-(trifluoromethyl)furan-3-carboxylate

생성물 1

HCID 27798975-Methyl-2-(trifluoromethyl)-3-furanmethanol수율 58.5%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To a solution of 5-methyl-2-trifluoromethyl-furan-3-carboxylic acid ethyl ester (0.83 g, 3.7 mmol) in Et2O at 0° C., was added DIBAL-H (1.0 M in THF, 1.5 mL). After 10 min, the ice bath was removed and additional DIBAL-H was added (1.0 M in THF, 14.5 mL). After 2 h, the reaction was quenched with a saturated solution of sodium potassium tartrate (aq.) and allowed to stir overnight. After 18 h, EtOAc was added and the organic layer separated and dried provide the title compound (0.39 g, 58%). 1H NMR (CDCl3): 6.19 (s, 1H), 4.62 (s, 2H), 2.36-2.28 (m, 3H).

후처리

  1. customthe ice bath was removed
  2. additionadditional DIBAL-H was added (1.0 M in THF, 14.5 mL)
  3. waitAfter 2 h
  4. customthe reaction was quenched with a saturated solution of sodium potassium tartrate (aq.)
  5. waitAfter 18 h
  6. additionEtOAc was added
  7. customthe organic layer separated
  8. customdried

출처 및 근거

ORD 기록
ord-8901ed5de1704aa69f65c3f13bdd6fe3
출처 데이터셋
uspto-grants-2014_02
특허 번호
US08642583B2

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