Sodium hydride → HCID 11690469, compound

HRID 1452610Notes

Reaction equation

[H-].[Na+].[CH3:3][C@@H:4]([OH:8])[C@H:5]([OH:7])[CH3:6].F[C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=1>C1COCC1>[CH3:3][C@H:4]([O:8][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:19])([F:21])[F:20])[CH:11]=1)[C@@H:5]([O:7][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[C:12]([C:18]([F:21])([F:20])[F:19])[CH:11]=1)[CH3:6]

Participants

Conditions

Temperature: 0 °C

Procedure

The NaH was suspended in 15 ml of dry THF at 0° C. under N2 gas, then (2R,3R)-2,3-butanediol (0.23 g, 2.46 mmol) was added, this mixture was stirred at 0° C. under N2 for 10 min before adding 4-fluoro-2-(trifluoromethyl)-benzonitrile (1.0 g, 5.18 mmol) The reaction mixture was stirred at 0° C. for 2 hours, then RT(room temperature) for 1 hour. It was quenched with 50 ml of distilled water, extracted with ethyl acetate (3×30 ml), the organic layer was washed with saturated NaHCO3 (three times), the solvent was removed to yield the crude product, it was purified by silica gel column with hexane:ethyl acetate=5:1 as the elute.

Workup

stirringwas stirred at 0° C. for 2 hours
waitRT(room temperature) for 1 hour
customIt was quenched with 50 ml of distilled water
extractionextracted with ethyl acetate (3×30 ml)
washthe organic layer was washed with saturated NaHCO3 (three times)
customthe solvent was removed

Sources & evidence

ORD record: ord-266030865b684994b145ea9aa8b07618
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07473711B2

Reaction notes

Loading…