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

HRID 237252ノート

反応式

HRID 237252 の反応式
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

参加物

4

反応物 2

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

生成物 1

HCID 27798975-Methyl-2-(trifluoromethyl)-3-furanmethanol収率 58.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-8901ed5de1704aa69f65c3f13bdd6fe3
出典データセット
uspto-grants-2014_02
特許番号
US08642583B2

反応ノート

読み込み中…