Water → HCID 86653778, compound

Participants

Reaction Conditions

Reaction Steps

2,5-Bis(benzyloxy)-3,4,6-trimethylbenzaldehyde (3.90 g, 12.16 mmol) was dissolved into 50 mL THF and cooled to 0° C. prior to the addition of 15 mL allyl Grignard (1.0 M in THF, 15 mmol). The pale yellow solution browned over the course of the addition. After 15 minutes at 0° C. the reaction was not complete by HPLC and an additional portion of allyl Grignard (3 mL, 1.0 M in THF, 3 mmol) was added and stirred for 0.6 h at which time the reaction was judged complete by HPLC. The reaction was treated carefully at 0° C. with 50 mL 10% aqueous NH4Cl stirred for five minutes post addition and 100 mL EtOAc added. The layers were stirred vigorously until they clarified, an additional 100 mL H2O and 100 ml EtOAc was added, the layers separated and the aqueous phase extracted 3×100 mL EtOAc. The combined organics were washed with 2×50 mL saturated aqueous NaCl and dried over Na2SO4 prior to concentration to a pale brown oil. Storage under vacuum gave a brown solid. Flash chromatography (gradient elution 0-20% EtOAc/heptane) yielded 3.91 g of 1-(2,5-bis(benzyloxy)-3,4,6-trimethylphenyl)but-3-en-1-ol as a white, waxy solid. M++H—H2O=385 m/z; 1H NMR (400 MHz, CDCl3) δ=7.55 (d, 4 H), 7.51-7.42 (m, 6 H), 5.91 (m, 1H), 5.19-5.10 (m, 3 H), 5.01 (d, 1 H), 4.90 (d, 1 H), 4.78 (s, 2 H), 3.35 (d, 1 H), 2.76 (m, 1 H), 2.55 (m, 1 H), 2.39 (s, 3 H), 2.32 (s, 3 H), 2.31 (s, 3 H) ppm.

Provenance & Evidence