Tetrahydrofuran → HCID 68294279, compound

Participants

Reaction Steps

To a solution of 314 (302 mg, 0.913 mmol) in tert-BuOH (20 mL) and H2O (5 mL) was added 2M solution of 2-methyl-2-butene in THF (4.56 mL, 9.13 mmol) then NaH2PO4 (1.204 g, 10.0 mmol). The reaction was stirred 5 min, then NaClO2 (495 mg, 5.48 mmol) was added and the reaction stirred at RT overnight. The reaction was partitioned between EtOAc (50 mL) and 0.5M HCl (30 mL), phases separated and the aqueous phase extracted with EtOAc (50 mL). The combined organic extracts were washed with satd. aq. NaCl (50 mL), dried (MgSO4), filtered and concentrated. The crude product was purified by SiO2 chromatography eluting with 10% EtOAc/hexane to afford 270 mg (85%) of 4-(tert-butyldimethylsilyloxy)-3-(3-chloro-4-fluorophenyl)butanoic acid (316) as a gray crystalline solid: 1H NMR (400 MHz, CDCl3) δ 7.27 (dd, J=2.3, 7.1 Hz, 1H), 7.08 (m, 2H), 3.74 (m, 1H), 3.61 (m, 1H), 3.26 (m, 1H), 2.91 (m, 1H), 2.61 (m, 1H), 0.86 (s, 9H), −0.03 (d, J=1.6 Hz, 6H); MS LRMS (APCI neg) m/e=345.1 (M−H).

Provenance & Evidence