Carbon Dioxide → HCID 14478664, compound

Temperature

-30 °C

A mixture of 2R 2-ethyl-2,3-epoxypropanol (2.6 g, 25.5 mmol) and copper iodide (475 mg, 2.5 mmol) was stirred in tetrahydrofuran (50 mL) under nitrogen and brought to -30° C. (dry ice, acetonitrile). Vinyl magnesium bromide [32 mL, 2M in tetrahydrofuran (THF), 2.5 eq] was added from a dropping funnel at such a rate as to maintain the temperature at -25° to -30° C. The reaction mixture was stirred at -30° C. for 2 h then brought to 0° C. and acidified with 10% HCl. The THF layer was separated and the aqueous phase was extracted with ether (3×50 mL). The organic layers were combined, dried over sodium sulfate, concentrated and distilled to give the title compound as a clear colorless oil (2.2 g, 60%, b.p. 85° C/5 mm). TLC Rf 0.26 (silica gel, 5% meOH in CH2Cl2, CAS/char:brown).

1. custombrought to -30° C.
2. temperatureto maintain the temperature at -25° to -30° C
3. customthen brought to 0° C.
4. customThe THF layer was separated
5. extractionthe aqueous phase was extracted with ether (3×50 mL)
6. dry with materialdried over sodium sulfate
7. concentrationconcentrated
8. distillationdistilled

ORD record

ord-11943e8c5e6744a8978cb4071832211f

Source dataset

uspto-grants-1990_01

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04897477