Diisopropylamine → HCID 18957380, compound

Participants

Reaction Conditions

Reaction Steps

A solution of methyl 3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]benzeneacetate (12.00 g, 43 mmol) in dry THF (40 mL) was added dropwise to a solution of LDA (prepared from nBuLi (20.70 mL of a 2.5 M solution, 3.32 g, 51 mmol) and iPr2NH (4.79 g, 6.60 mL, 47 mmol)) in THF (300 mL) maintained at about -78° C. under an atmosphere of N2. After about 15 minutes, 2-bromomethyl-4,5-diphenyloxazole (14.86 g, 47 mmol) in THF (20 mL) was added dropwise. The mixture was stirred for about 30 minutes at about -78° C., poured onto saturated NH4Cl solution and extracted with CH2Cl2. The combined extracts were dried over Na2SO4, concentrated and the residual oil chromatographed on a column of silica gel. Elution with a mixture of hexanes and Et2O (9:1) gave methyl α -[3-[[(1,1-dimethylethyl)dimethylsilyl]oxy]phenyl]-4,5-diphenyl-2-oxazolepropanoate (12.40 g, 56%) 1H NMR (CDCl3) δ0.18 (6H, s, Si(CH3)2), 0.98 (9H, s, (CH3)3C), 3.23 and 3.65 (2H, d of ABq, J=16 Hz, J'=8 Hz, CH2 -oxazole), 3.72 (3H, s, CO2CHH3), 4.29 (1H, dd, J=8 Hz, CHCO2CH3), 6.77 (1H, d, J=9 Hz, aromatic H), 6.88 (1H, s, aromatic H), 6.98 (1H, d, J=9 Hz, aromatic H), 7.20 (1H, t, J=8Hz, aromatic H), 7.25 to 7.45 (6H, m, aromatic H), 7.45 to 7.70 (4H, m, aromatic H).

Provenance & Evidence