tert-Butyl methyl ether → HCID 14376544, compound

A 3.5 L reactor equipped with a mechanical stirrer, a Pt-100 thermometer and a nitrogen inlet was charged with 127 g (731 mmol) 1,3-diacetoxyacetone, 1.95 L TBME and 309 g (877 mmol) carbethoxymethylene triphenylphosphorane. The solution was refluxed for 5 h, then allowed to cool to RT during 14 h. Then TBME was exchanged with 2.3 L heptane at 40° C./300 mbar and the mixture was stirred overnight at RT before 400 ml toluene was added. The suspension was stirred for 1 h at RT, then 2 h at 0-4° C., filtered, and the filter cake was washed portionwise with totally 600 ml pre-cooled toluene. The combined filtrates were concentrated on a rotatory evaporator at 45° C./10 mbar to give 193 g crude product as reddish oil. This material was dissolved in 200 ml of a heptane/ethyl acetate (3:1) mixture and was chromatographically filtered over a column containing 400 g silica gel 60 using heptane/ethyl acetate (3:1) as the eluent, to give 174 g 4-acetoxy-3-acetoxymethyl-but-2-enoic acid ethyl ester (98% yield; assay: 99.9%) as a colorless oil.

1. customA 3.5 L reactor equipped with a mechanical stirrer
2. temperatureThe solution was refluxed for 5 h
3. additionwas added
4. filtration2 h at 0-4° C., filtered
5. washthe filter cake was washed portionwise with totally 600 ml
6. temperaturepre-cooled toluene
7. concentrationThe combined filtrates were concentrated on a rotatory evaporator at 45° C./10 mbar
8. customto give 193 g crude product as reddish oil
9. filtrationwas chromatographically filtered over a column
10. additioncontaining 400 g silica gel 60 using heptane/ethyl acetate (3:1) as the eluent

ORD record

ord-a60c948b123a4ec1840414154fde2ed7

Source dataset

uspto-grants-2009_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07619101B2