4-Methyl-5-(2-hydroxyethyl)thiazole → HCID 68327671, compound

Participants

Reaction Conditions

Reaction Steps

An oven-dried 100 mL round bottom flask was charged with t-BuOK (20.8 mmol), dry THF (25 mL), purged with argon and cooled to 0° C. in an ice bath. 5-(2-Hydroxyethyl)-4-methylthiazole (16 mmol) was then added dropwise to the solution and the reaction stirred at 0° C. for 1 h under argon. Allyl bromide (20.8 mmol) was added dropwise, and the solution was warmed to R.T. and allowed to stir for 20 h under argon. Deionized water (4 mL) was then added and the reaction stirred for 10 min. All liquid were then removed in vacuo and the residue redissolved in ethyl acetate (50 mL). The organic phase was washed three times with water (20 mL), dried over Na2SO4, filtered over Celite, and then concentrated in vacuo to yield a yellow oil (96%). 1HNMR (400 MHz, CDCl3): δ=8.52 (s, 1H), 5.89 (m, 1H), 5.23 (dd, 1H, 3JHHtrans=17.4 Hz, 2JHHgems=1.8 Hz), 5.13 (dd, 1H, 3JHHcis=10.3 Hz, 2JHHgems=1.6 Hz), 3.96 (dt, 2H, 3JHH=5.7 Hz, 4JHH=1.4 Hz), 3.57 (t, 2H, 3JHH=6.9 Hz), 2.99 (t, 2H, 3JHH=6.9 Hz), 2.37 (s, 3H) ppm. 13CNMR (400 MHz, CDCl3): δ=149.6, 149.2, 134.5, 127.9, 17.0, 71.9, 70.0, 27.0, 14.9 ppm. HRMS-ESI: Calculated [M+H]+: 184.0791. found: 184.0787.

Provenance & Evidence