Methanol → (S)-Cyclopent-1-enyl-hydroxyphenylacetic acid

HRID 1505146ノート

反応式

HRID 1505146 の反応式
C([C@H]1[O:9][C:8](=[O:10])[C@:7]([C:17]2[CH2:21][CH2:20][CH2:19][CH:18]=2)([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[O:6]1)(C)(C)C.CO.O.[OH-].[K+].[Cl-].[NH4+]>>[C:17]1([C@:7]([OH:6])([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)[C:8]([OH:10])=[O:9])[CH2:21][CH2:20][CH2:19][CH:18]=1

参加物

6

反応物 5

HCID 887MethanolHCID 962WaterHCID 14797Potassium HydroxideHCID 25517Ammonium ChlorideHCID 67242157(2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-one

生成物 1

HCID 67241271(S)-Cyclopent-1-enyl-hydroxyphenylacetic acid収率 69.9%

反応条件

温度
130 °C

実験手順

Intermediate (1c) (540 mg, 1.9 mmol) was dissolved in MeOH (927 μL, 22.9 mmol). Water (1.84 mL, 102 mmol) was added, followed by the addition of KOH (1.1 g, 18.8 mmol). The mixture was refluxed at 130° C. for 3 hours, followed by dilution to 250 mL with saturated ammonium chloride, then washed (2×100 mL hexane). The remaining aqueous emulsion was washed (2×250 mL EtOAc). The EtOAc layers were combined, washed with 50 mL saturated aqueous NaCl, dried over Na2SO4, filtered and concentrated to yield intermediate (1d) as a brownish-yellow solid (290 mg).

後処理

  1. washwashed (2×100 mL hexane)
  2. washThe remaining aqueous emulsion was washed (2×250 mL EtOAc)
  3. washwashed with 50 mL saturated aqueous NaCl
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-0906efbae1e94eff94c308edf9f4f1d9
出典データセット
uspto-grants-2015_12
特許番号
US09216971B2

反応ノート

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