Chloroacetaldehyde → (2-Trifluoromethyl-furan-3-yl)-methanol

HRID 1654115Notes

Reaction equation

HRID 1654115 reaction equation
Cl[CH2:2][CH:3]=O.[F:5][C:6]([F:16])([F:15])[C:7](=[O:14])[CH2:8][C:9]([O:11]CC)=O.Cl>N1C=CC=CC=1>[F:16][C:6]([F:5])([F:15])[C:7]1[O:14][CH:2]=[CH:3][C:8]=1[CH2:9][OH:11]

Participants

5

Reactant 3

HCID 33ChloroacetaldehydeHCID 313Hydrochloric AcidHCID 67793Ethyl 4,4,4-trifluoroacetoacetate

Product 1

HCID 17953606(2-Trifluoromethyl-furan-3-yl)-methanol

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

210 ml of chloroacetaldehyde were added over 30 minutes at 20° C. to 36.5 ml of ethyl 4,4,4-trifluoroacetoacetate in 600 ml of pyridine and the mixture was stirred for 52 hours. The reaction mixture was poured into 650 ml of concentrated hydrochloric acid and ice, stirred for 5 minutes and extracted with isopropyl ether. The extract was dried and the solvent was evaporated to obtain after chromatography on silica (eluent: 7/3 hexane/ethyl acetate), 43 g of the expected product.

Workup

  1. stirringstirred for 5 minutes
  2. extractionextracted with isopropyl ether
  3. customThe extract was dried
  4. customthe solvent was evaporated

Sources & evidence

ORD record
ord-9e1360cf4dc74a8d8fd4abed5b8dd2e1
Source dataset
uspto-grants-1995_04
Patent number
US05405865

Reaction notes

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