Sodium Hydroxide → HCID 86742441, compound

Participants

Reaction Steps

A solution of the compound (1h) (900 mg 1.7 mmol), 1 N NaOH (2.5 mL, 2.5 mmol) and MeOH (15 mL) was stirred at 25° C. for 1 hour. The reaction mixture was evaporated in vacuo at 25° C. and the residue was dissolved in H2O (100 mL). The reaction solvent was acidified with 12 N HCl (1 mL) and extracted with Et2O (100 mL). The organic extract was washed with H2O (2×100 mL), dried over MgSO4, filtered, evaporated and the residual crude dihydroxy acid was dissolved in toluene (75 mL) and heated at reflux in a Dean-Stark apparatus. After 3 hours the toluene was removed in vacuo leaving the crude compound (1i) as a thick yellow oil. The oil was chromatographed on silica gel. Elution with CH2Cl2 -acetone (19:1, v=v) to provide the compound (1i) as a pale yellow oil, homogenous by HPLC [time of elution was 3.72 minutes with a flow rate of 4 mL/minutes using 10% isopropanol/hexane on a Whatman Partisil PXS 10/25 PAC column]; NMR 0.139 (6H, s), 0.946 (9H, s), 1.61-1.84 (2H, m), 2.345 (6H, s), 2.45-2.75 (2H, m), 3.947-3.994 (H, m), 4.81 (2H, m), 5.096-5.134 (H, m), 5.30 (H, dd, J=7 and 16 Hz), 6.50 (H, d, J=16 Hz), 6.938-7.338 (6H, m).

Provenance & Evidence