Water → (Z)-3-(2-(Isopropoxycarbonyl)-3-(trifluoromethyl)phenyl)acrylic acid

HRID 2100571노트

반응식

HRID 2100571 반응식
C[O:2][C:3](=[O:22])/[CH:4]=[CH:5]\[C:6]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[C:7]=1[C:8]([O:10][CH:11]([CH3:13])[CH3:12])=[O:9].O.[OH-].[Li+].C([O-])([O-])=O.[Na+].[Na+]>C1COCC1.C([O-])(O)=O.[Na+]>[CH:11]([O:10][C:8]([C:7]1[C:14]([C:18]([F:19])([F:21])[F:20])=[CH:15][CH:16]=[CH:17][C:6]=1/[CH:5]=[CH:4]\[C:3]([OH:22])=[O:2])=[O:9])([CH3:13])[CH3:12]

참가 물질

7

반응물 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 10340Sodium CarbonateHCID 69052122HCID 69052122, 화합물

생성물 1

HCID 69056742(Z)-3-(2-(Isopropoxycarbonyl)-3-(trifluoromethyl)phenyl)acrylic acid수율 92%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 516892Sodium Bicarbonate용매

실험 절차

To a solution of (Z)-isopropyl 2-(3-methoxy-3-oxoprop-1-enyl)-6-(trifluoromethyl)benzoate from Example 1, Part D (1.88 g, 5.94 mmol) in 20 mL of THF and 10 mL of water was added lithium hydroxide (157 mg, 6.53 mmol). The reaction was allowed to stir at ambient temperature for 3 h. The reaction was diluted with sat'd aq NaHCO3 and sat'd aq Na2CO3 to pH 8-9 and extracted with 1:1 hexane/ethyl acetate. The organics were discarded. The aqueous layer was acidified carefully with conc. HCl and extracted with ethyl acetate. The ethyl acetate layer was washed with brine, dried (MgSO4) and concentrated in vacuo to afford 1.65 g (92%) of the title compound as a white solid. 1H NMR (CDCl3): δ 7.65 (d, 1H, J=7.7 Hz), 7.60 (d, 1H, J=7.7 Hz), 7.48 (t, 1H, J=7.7 Hz), 7.19 (d, 1H, J=12.1 Hz), 6.09 (d, 1H, J=12.1 Hz), 5.25 (septet, 1H), 1.32 (d, 6H, J=6.1 Hz). LRMS (ESI): 325.19 (M+H+Na)+.

후처리

  1. extractionextracted with 1:1 hexane/ethyl acetate
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer was washed with brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

출처 및 근거

ORD 기록
ord-eb6c6816ee864c0faacd6d570659d787
출처 데이터셋
uspto-grants-2009_08
특허 번호
US07572805B2

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