Trimethyl orthoformate → HCID 178502927, compound

Trimethyl orthoformate (11.0 mL, 10.7 g, 101 mmol) was added to anhydrous hypophosphorous acid3 (4.0 mL, 6.0 g. 90 mmol) and the solution was stirred for 1.5 h at room temperature. In a separate flask, N,N,N',N'-tetramethylguanidine (1.50 mL, 1.38 g, 12.0 mmol) was added to benzyl 2-methylene-4-phenyl-butanoate (3.99 g, 15.0 mmol) and the solution was cooled to 0° C. by an ice bath. An portion of the methyl hypophosphite solution (12.0 mL, d=1.04 g/mL, approx. 68 mmol) was added over 1 h. The ice bath was removed and the solution was stirred an additional 1.25 h. The reaction was diluted with ethyl acetate (150 mL) and washed with 2N aqueous hydrochloric acid (50 mL), water (50 mL), and saturated aqueous sodium chloride (50 mL). The aqueous layers were extracted in succession with ethyl acetate (50 mL). The organic layers were dried (sodium sulfate), decanted, and evaporated. After drying overnight under vacuum, the crude product was 5.19 g (100% yield) of viscous colorless oil.

1. temperaturethe solution was cooled to 0° C. by an ice bath
2. customThe ice bath was removed
3. stirringthe solution was stirred an additional 1.25 h
4. additionThe reaction was diluted with ethyl acetate (150 mL)
5. washwashed with 2N aqueous hydrochloric acid (50 mL), water (50 mL), and saturated aqueous sodium chloride (50 mL)
6. extractionThe aqueous layers were extracted in succession with ethyl acetate (50 mL)
7. dry with materialThe organic layers were dried (sodium sulfate)
8. customdecanted
9. customevaporated
10. customAfter drying overnight under vacuum

ORD record

ord-670d1ce3fa5440b9b27030ff29a5c833

Source dataset

uspto-grants-1997_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05679700