Ethylacetate heptane → HCID 24755603, compound

Participants

Reaction Steps

To a cooled (˜5° C.) solution of methylmagnesium chloride (3M in THF; 81.3 mL, 244 mmol, 10 equiv.) in tetrahydrofuran (116 mL), was added a solution of compound 4 (6.5 g, 24.4 mmol) in tetrahydrofuran (348 mL) drop-wise, over ninety minutes, keeping the temperature at about 0° C. by the rate of addition. A bright yellow solution was observed on addition. After one hour, TLC (ethyl acetate/n-heptane 1/1) showed no starting material present and a new spot moving at a lower Rf. The batch was quenched by the careful addition of a saturated, aqueous solution of sodium bicarbonate (about 660 mL). A thick mass ensued and ethyl acetate (250 mL) and water (250 mL) were added to the mixture. The aqueous layer was removed and re-extracted with ethyl acetate (2×250 mL). The ethyl acetate fractions were combined, washed with water (2×200 mL) and concentrated on the Buchi at a bath temperature of 40° C. and from 80 to 10 torr, to give 7.5 g (109%) of 1 as a light-beige solid: 1H NMR (DMSO-d6, FIG. 2) δ 12.0 (1H, s), 8.35 (1H, d, J=3.5 Hz), 8.2 (1H, d, J=3.5 Hz), 7.6 (4H, s), 5.1 (1H, s), 2.9 (2H, q, J=8 Hz), 1.5 (6H, s), 1.3 (3H, t, J=8 Hz).

Provenance & Evidence