5-(Difluoromethyl)furan-2-carbaldehyde → 2-Furanmethanol, 5-(difluoromethyl)-alpha-ethynyl-

HRID 1654107Notes

Reaction equation

[C:1]([Mg]Br)#[CH:2].[F:5][CH:6]([F:14])[C:7]1[O:11][C:10]([CH:12]=[O:13])=[CH:9][CH:8]=1.P([O-])(O)(O)=O.[Na+]>O1CCCC1>[F:5][CH:6]([F:14])[C:7]1[O:11][C:10]([CH:12]([OH:13])[C:1]#[CH:2])=[CH:9][CH:8]=1

Participants

Conditions

Temperature: 0 °C

Procedure

43 ml of a 0.5M solution of ethynyl magnesium bromide in tetrahydrofuran were added at 0° C. over one hour to a solution of 2.5 g of the product of Stage A and 30 ml of tetrahydrofuran. The reaction mixture was stirred at 0° C. for 1 hour and then was poured into a saturated aqueous sodium dihydrogenphosphate solution. The 3 g of product were chromatographed on silica by eluting with a 7/3 hexane/ethyl acetate mixture to obtain 2.5 g of the desired product.

Workup

customThe 3 g of product were chromatographed on silica
washby eluting with a 7/3 hexane/ethyl acetate mixture

Sources & evidence

ORD record: ord-9687eb84b4484ce5bb90b631d8726245
Source dataset: uspto-grants-1995_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05405865

Reaction notes

Loading…