Hydrogen Bromide → 2-Bromo-1-(5-methyloxolan-2-yl)ethan-1-one

A solution of 5-methyl-2-tetrahydrofuroic acid (1.80 g, 13.85 mmol) in dichloromethane (25 ml) was treated with oxalyl chloride (2.4 ml, 27.51 mmol) in the presence of dimethylformamide (3 drops). After stirring for 1.25 h, the solvent was evaporated in vacuo. The residue was re-dissolved in dichloromethane and concentrated again. Excess diazomethane was then bubbled through a solution of the resulting acid chloride in dichloromethane (30 ml) at 0° C. When the addition was complete, the mixture was stirred for 10 min. at 0° C. and then treated with 48% aqueous hydrogen bromide (2.6 ml, 15.41 mmol). The mixture was stirred for 15 min. at room temperature, washed with water (x2), dried and concentrated in vacuo to yield the crude title compound as a brown oil (1.67 g, 58%); νmax (CH2Cl2) 1735, 1387 and 1086 cm-1 ; δH (CDCl3, 90 MHz) 1.33 (3 H, d, J 6.0 Hz), 1.48 (1 H, m), 1.90-2.35 (3 H, m), 4.10 (1 H, m), 4.25 (2 H, s) and 4.48 (1 H, m).

1. customthe solvent was evaporated in vacuo
2. dissolutionThe residue was re-dissolved in dichloromethane
3. concentrationconcentrated again
4. customExcess diazomethane was then bubbled through a solution of the resulting acid chloride in dichloromethane (30 ml) at 0° C
5. additionWhen the addition
6. stirringthe mixture was stirred for 10 min. at 0° C.
7. stirringThe mixture was stirred for 15 min. at room temperature
8. washwashed with water (x2)
9. customdried
10. concentrationconcentrated in vacuo

ORD record

ord-b63e5fa24b684a5f8d008632d1377ed5

Source dataset

uspto-grants-1999_12

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06001997