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

HRID 351229ノート

反応式

HRID 351229 の反応式
[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

参加物

5

反応物 3

HCID 737671-(Trifluoroacetyl)imidazoleHCID 78246p-BenzyloxypropiophenoneHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 210906931-[4-(Benzyloxy)phenyl]-4,4,4-trifluoro-2-methyl-1,3-butanedione

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-60 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-037b7ae049d84577b6d7928f0a4ba1fb
出典データセット
uspto-grants-2007_02
特許番号
US07183306B2

反応ノート

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