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

HRID 2100571ノート

反応式

HRID 2100571 の反応式
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]

参加物

7

反応物 4

HCID 962WaterHCID 3939Lithium HydroxideHCID 10340Sodium CarbonateHCID 69052122HCID 69052122、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

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)+.

後処理

  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

出典と根拠

ORDレコード
ord-eb6c6816ee864c0faacd6d570659d787
出典データセット
uspto-grants-2009_08
特許番号
US07572805B2

反応ノート

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