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

HRID 2097685노트

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HRID 2097685 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 25517Ammonium Chloride용매

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온도
130 °C

실험 절차

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 reaction was refluxed at 130° C. for 3 hours. The mixture was diluted 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).

후처리

  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

출처 및 근거

ORD 기록
ord-1a3075292cef4e4ca3b369b85a829131
출처 데이터셋
uspto-grants-2013_05
특허 번호
US08450362B2

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