1-(Trifluoroacetyl)imidazole → 1-[4-(Benzyloxy)phenyl]-4,4,4-trifluoro-2-methyl-1,3-butanedione

HRID 351229Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([C:15](=[O:18])[CH2:16][CH3:17])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[F:29][C:30]([F:39])([F:38])[C:31](N1C=CN=C1)=[O:32]>C1COCC1>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([C:15](=[O:18])[CH:16]([CH3:17])[C:31](=[O:32])[C:30]([F:29])([F:38])[F:39])=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of 4′-benzyloxypropiophenone (6.0 g) in THF (120 ml) at −60° C. was added 38 ml of 1N lithium bis(trimethylsilyl)amide (LiHMDS), and the mixture was stirred at under −60° C. for 45 mins. 1-(Trifluoroacetyl)-imidazole (3.4 ml) was added and the mixture was stirred at −60° C. for 1 hour and at 0° C. for 30 min. The raction mixture was quenched with 0.5N HCl, the mixture was poured into EtOAc and water, and the EtOAc layer was separated, washed with brine, died over MgSO4, and concentrated to give 1-[4-(benzyloxy)phenyl]-4,4,4-trifluoro-2-methyl-1,3-butanedione.

Workup

stirringthe mixture was stirred at −60° C. for 1 hour and at 0° C. for 30 min
customThe raction mixture was quenched with 0.5N HCl
additionthe mixture was poured into EtOAc and water
customthe EtOAc layer was separated
washwashed with brine
concentrationconcentrated

Sources & evidence

ORD record: ord-037b7ae049d84577b6d7928f0a4ba1fb
Source dataset: uspto-grants-2007_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07183306B2

Reaction notes

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