Tetrahydrofuran → 5-Carbomethoxy-5-methyl-1,3-dioxan-2-one

Temperature

-78 °C

In a 500 mL three neck RB flask were added methyl 2,2-bis(hydroxymethyl)propionate (12.45 g) and tetrahydrofuran (THF) (100 mL). The resulting mixture was stirred under nitrogen via a mechanical stirrer until a homogeneous solution results. Triphosgene (8.78 g) was added and the solution cooled to −78° C. Triethylamine (18.3 g) was slowly added to the cooled solution. The resulting mixture was stirred at this temperature for one hour and then allowed to warm to room temperature. The triethylamine/HCl salt was filtered off and the resulting filtrate pass through a shallow bed of silica gel. The filtrate was concentrated at reduced pressure and then dried under vacuum affording 13.4 g of product which had a small amount of contamination. This contamination was removed via washing with warm diethyl ether. 1H NMR (CDCl3) ppm: 4.67 (ab doublet, 2H), 4.20 (ab doublet, 2H), 3.77 (S, 3H), 1.30 (S, 3H).

1. customresults
2. stirringThe resulting mixture was stirred at this temperature for one hour
3. temperatureto warm to room temperature
4. filtrationThe triethylamine/HCl salt was filtered off
5. concentrationThe filtrate was concentrated at reduced pressure
6. customdried under vacuum

ORD record

ord-c6b2998b0e5b4f3d9ce5bca9da92ed96

Source dataset

uspto-grants-2001_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06228979B1