Hydrochloric Acid → HCID 59913127, compound

Temperature

0 °C

iso-Butylchloroformate (6.83 g, 50.0 mmol) was added to a solution of itaconic acid mono-n-butyl ester (9.31 g, 50.0 mmol) and triethylamine (5.06 g, 50.0 mmol) in THF (40 mL) under a nitrogen atmosphere and cooled to 0° C. The reaction was stirred for 0.5 h, filtered to remove the solids, added to a solution of sodium borohydride (3.78 g, 100.0 mmol) in water (20 mL), and cooled to 10° C. The reaction was stirred for 2 h, made acidic with 3 N HCl and extracted with ethyl ether (3×). The combined organic layers were washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel, eluting ethyl acetate:hexanes (1:2) to give 3-hydroxymethyl-but-3-enoic acid butyl ester (2.56 g, 30%) as an oil. MS found: (M+H)+=173.

1. filtrationfiltered
2. customto remove the solids
3. temperaturecooled to 10° C
4. stirringThe reaction was stirred for 2 h
5. extractionextracted with ethyl ether (3×)
6. washThe combined organic layers were washed with brine
7. dry with materialdried over magnesium sulfate
8. concentrationconcentrated
9. customto give an oil
10. customThe product was purified by FCC on silica gel
11. washeluting ethyl acetate:hexanes (1:2)

ORD record

ord-31c0175abff84d42bc8f1284a4c637de

Source dataset

uspto-grants-2006_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07125870B2