Toluene → HCID 86758778, compound

To a suspension of methyltriphenylphosphonium bromide (5.2 g, 14.5 mmol) in anhydrous dioxane (75 mL) at room temperature under a nitrogen atmosphere, a 0.5M solution of potassium bis(trimethylsilyl)amide in toluene (24.4 mL, 12.2 mmol) was added. After 1 hour, the mixture was added via cannula to a solution ethyl (1RS,5SR,6RS)-2-hydroxy-3-oxabicyclo[3.1.0]-hexane-6-carboxylate (1.0 g, 2.62 mmol) in anhydrous dioxane (25 mL) under a nitrogen atmosphere and the reaction mixture was stirred for 1 hour. Then, the mixture was poured onto a 2:1 mixture of diethyl ether and water (300 mL) and the layers were separated. The aqueous layer was extracted with diethyl ether (2×100 mL) and the combined organic layers were dried over sodium sulfate, filtered and concentrated to dryness. The residue was purified by column chromatography using ethyl acetate and hexane 1:2 as eluent to afford 840 mg (85% yield) of ethyl (1SR,2SR,3RS)-2-hydroxymethyl-3-vinylcyclopropane carboxylate.

1. customthe layers were separated
2. extractionThe aqueous layer was extracted with diethyl ether (2×100 mL)
3. dry with materialthe combined organic layers were dried over sodium sulfate
4. filtrationfiltered
5. concentrationconcentrated to dryness
6. customThe residue was purified by column chromatography

ORD record

ord-eabd8ac69906416995b060c99dccf7f8

Source dataset

uspto-grants-2003_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06504052B1