Methanol → HCID 22872579, compound

A solution of 6.8 g (20 mmol) of 3(2(R),3(S),7-trimethyl-6-octenoyl)-4(R)-phenylmethyl-2-oxazolidinone in 30 mL of THF was added dropwise to a suspension of 1.634 g (43 mmol) of lithium aluminum hydride in 40 mL of THF at 0° C. The reaction mixture was then stirred 6 h at ambient temperature The reaction mixture was then recooled in ice bath and 5 mL of methanol was added dropwise very cautiously. After the effervescence subsided, the reaction mixture was concentrated to about 30% of the original volume The reaction mixture was then stirred with saturated solution of potassium sodium tartrate and extracted with ethyl acetate. The combined ethyl acetate extracts were dried over anhydrous magnesium sulfate. Solvent removal afforded a crude oil, which was purified on silica gel using 10% ethyl acetate in hexane as solvent to give 2.0 g (62%) of the desired alcohol as a colorless oil.

1. concentrationthe reaction mixture was concentrated to about 30% of the original volume The reaction mixture
2. stirringwas then stirred with saturated solution of potassium sodium tartrate
3. extractionextracted with ethyl acetate
4. dry with materialThe combined ethyl acetate extracts were dried over anhydrous magnesium sulfate
5. customSolvent removal
6. customafforded a crude oil, which
7. customwas purified on silica gel using 10% ethyl acetate in hexane as solvent

ORD record

ord-0275f3f5050c4ecba16e03a27d4c016b

Source dataset

uspto-grants-1997_05

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05629322