Oxalyl chloride → HCID 18780160, compound

A solution of (2RS,5SR)-5-methoxymethyltetrahydrofuran-2-carboxylic acid (3.1 g) in dichloromethane (50 ml) was treated with oxalyl chloride (2.68 ml) and dimethylformamide (1 drop). The mixture was stirred for 1 h and heated to reflux for 10 mins. The solvent was evaporated and then dichloromethane was evaporated from the residue twice. The product was dissolved in dichloromethane (100 ml) and the solution cooled in an ice bath. Diazomethane was then passed into the solution as described in Example 14(a). When the addition was complete the mixture was stirred at 0° C. for 0.5 h and then hydrogen chloride gas was passed into the solution until all the diazoketone had been consumed. The solution was washed with brine, dried over magnesium sulphate and evaporated. The title compound (2.44 g) was isolated by column chromatography using gradient elution (silica gel, 4:1 going to 1:1 hexane:ethyl acetate); νmax (film) 1740 cm-1 ; δH (CDCl3) 1.6-2.35 (4H,m), 3.30-3.75 (2H,m), 3.37 (3H,s) and 4.05-4.75 (4H,m).

1. temperatureheated
2. temperatureto reflux for 10 mins
3. customThe solvent was evaporated
4. customdichloromethane was evaporated from the residue twice
5. dissolutionThe product was dissolved in dichloromethane (100 ml)
6. temperaturethe solution cooled in an ice bath
7. additionWhen the addition
8. stirringwas stirred at 0° C. for 0.5 h
9. customhad been consumed
10. washThe solution was washed with brine
11. dry with materialdried over magnesium sulphate
12. customevaporated

ORD record

ord-1f74e5594561430ca83e2ec5a2479538

Source dataset

uspto-grants-2000_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06077952