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

HRID 237252Notes

Reaction equation

HRID 237252 reaction equation
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

Participants

4

Reactant 2

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-8901ed5de1704aa69f65c3f13bdd6fe3
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

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