Triphenylphosphine → HCID 136340744, compound

Participants

Reaction Steps

--Quantities: hydroxy acid 59 (716 mg, 3.28 mmol), DEAD (572 mg, 3.28 mmol), triphenylphosphine (861 mg, 3.28 mmol), (R)-(-)-octan-2-ol (428 mg, 3.28 mmol), THF (100 ml). The experimental procedure was as described for compound 47. Flash chromatography (10% ethyl acetate-light petroleum) gave the 1-methylheptyl ester 60 (520 mg, 48%) (from EtOH/AcOH), m.p.98.8° C., [α]D22 +44.7° (c 1.7 in CHCl3); νmax /cm-1 (KBr) 3440br, 2920, 1670, 1570, 1430, 1345, 1300, 1165 and 810; δ 0.88 (3H, t), 1.20-1.50 (11H, m), 1.70 (2H, m, CH2CHMe), 5.22 (1H, sext, OCHMe), 6.10 (1H, br s), 6.94 (2H, d, 3'- and 5'-H), 8.42 (2H, d, 2'- and 6'-H) and 9.27 (2H s, 4- and 6-H); m/z 328 (M+),314, 285, 261, 247 216 and 119.

Provenance & Evidence