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

HRID 1505146Notes

Reaction equation

HRID 1505146 reaction equation
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

Participants

6

Reactant 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

Product 1

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

Conditions

Temperature
130 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-0906efbae1e94eff94c308edf9f4f1d9
Source dataset
uspto-grants-2015_12
Patent number
US09216971B2

Reaction notes

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