Methanol → HCID 22723509, compound

To the reaction mixture obtained in Example 2 were added 10% aqueous sodium hydroxide solution (113.8 g) and methanol (20 mL), and the mixture was stirred at room temperature overnight. The disappearance of tert-butyl 4-cyano-3-hydroxy-4-methylpentanoate was confirmed by gas chromatography (GC). Toluene (50 mL) was added and the mixture was stirred and then partitioned to remove the toluene layer. 20% Aqueous hydrochloric acid solution (67.5 g) was added to the aqueous layer to adjust its pH to an acidic one (ca. pH 1-2) and the mixture was extracted twice with ethyl acetate (150 mL). The ethyl acetate layer was concentrated under reduced pressure to give 4-cyano-3-hydroxy-4-methylpentanoic acid (19.9 g) as an oil. When left standing, this oil crystallized. The yield was 89% relative to tert-butyl 4-cyano-3-hydroxy-4-methylpentanoate.

1. stirringthe mixture was stirred
2. custompartitioned
3. customto remove the toluene layer
4. addition20% Aqueous hydrochloric acid solution (67.5 g) was added to the aqueous layer
5. extractionthe mixture was extracted twice with ethyl acetate (150 mL)
6. concentrationThe ethyl acetate layer was concentrated under reduced pressure

ORD record

ord-efc91ddd0ea74472842ff9880b877bab

Source dataset

uspto-grants-2004_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06730803B2