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

Participants

Role	Name	HCID	Charge
Reactant	Methanol	HCID 887	—
Reactant	Water	HCID 962	—
Reactant	Potassium Hydroxide	HCID 14797	—
Reactant	Ammonium Chloride	HCID 25517	—
Reactant	(2R,5S)-2-t-Butyl-5-cyclopent-1-enyl-5-phenyl-1,3-dioxolan-4-one	HCID 67242157	—
Product	(S)-Cyclopent-1-enyl-hydroxyphenylacetic acid	HCID 67241271	69.9%

Reaction Conditions

Temperature	130 °C

Reaction Steps

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).

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US09216971B2
Source dataset	uspto-grants-2015_12
ORD ID	ord-0906efbae1e94eff94c308edf9f4f1d9
Source note	uspto-grants-2015_12