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

HRID 351229노트

반응식

HRID 351229 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-60 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-037b7ae049d84577b6d7928f0a4ba1fb
출처 데이터셋
uspto-grants-2007_02
특허 번호
US07183306B2

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