Ethyl 2-(trifluoromethyl)furan-3-carboxylate → (2-Trifluoromethyl-furan-3-yl)-methanol

HRID 1654117Notes

Reaction equation

HRID 1654117 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[C:8](OCC)=[O:9].[H-].C([Al+]CC(C)C)C(C)C.[K].[Na]>C1(C)C=CC=CC=1>[F:14][C:2]([F:1])([F:13])[C:3]1[O:4][CH:5]=[CH:6][C:7]=1[CH2:8][OH:9]

Participants

5

Reactant 3

HCID 4737733Ethyl 2-(trifluoromethyl)furan-3-carboxylateHCID 16211683Potassium alloy, nonbase, K,NaHCID 21225700Diisobutylaluminumhydride

Product 1

HCID 17953606(2-Trifluoromethyl-furan-3-yl)-methanolYield 100.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
-60 °C

Procedure

20 g of the product of Stage B were cooled to -60° C. in 200 ml of toluene, 160 ml of diisobutylaluminium hydride were added dropwise. The mixture was stirred for 1 and a half hours at -60° C. and was then poured into sodium potassium double tartrate and extracted with methylene chloride. The solvent was evaporated and the residue was chromatographed on silica (eluent: 7/3 hexane/ethyl acetate) to obtain 16 g of the expected product.

Workup

  1. extractionextracted with methylene chloride
  2. customThe solvent was evaporated
  3. customthe residue was chromatographed on silica (eluent: 7/3 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-2dc7d959de834299be269f9424b9cc89
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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