Potassium Sodium Tartrate → HCID 12927274, compound

Participants

Reaction Conditions

Reaction Steps

Diisobutyl aluminum hydride (1 M in CH2Cl2, 27.5 mL, 27.5 mmol,) was slowly added to a cold solution (−78° C.) of ethyl (2Z)-3-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2-propenoate 4, (2.50 g, 12.5 mmol) in dichloromethane (30 mL). The solution was allowed to stir for 15 min at −78° C. (a color change from colorless to yellow and back to colorless indicates that the reaction is complete). A saturated solution of Rochelle's salt (20 mL) was added and the reaction mixture was warmed to room temperature. The reaction was stirred until both layers were clear. The organic layer was separated and the aqueous layer was extracted with dichloromethane (3×15 mL). The organic layers were combined, washed with brine and dried over MgSO4. The solid was filtered out and the organic layer was concentrated under vacuum. The crude mixture was purified on silica gel using 20% ethyl acetate/hexanes to obtain alcohol 5 (1.9 g, 95% yield) as a colorless oil. Rf=0.27 (40% ethyl acetate/hexanes). 1H NMR (400 MHz, CDCl3): δ 5.84-5.81 (m, 1H), 5.55 (t, J=8.5 Hz, 1H), 4.85 (q, J=9.6 Hz, 1H), 4.28 (dd, J=6.8, 7.3 Hz, 1H), 4.18 (d, J=4.8 Hz, 1H), 4.08 (t, J=6.5 Hz, 1H), 3.56 (t, J=9.0 Hz, 1H), 2.12 (bs, 1H), 1.41 (s, 3H), 1.38 (s, 3H). 13C NMR (100 MHz, CDCl3): δ 133.1, 129.4, 109.4, 71.8, 69.4, 58.5, 26.6, 25.8

Provenance & Evidence