tert-Butyl acetate → HCID 14852352, compound

n-BuLi (1.6M, 6 ml) was added over 5 min. to a stirred, cooled (-10°) solution of cyclohexylisopropylamine (1.64 ml) in dry THF (10 ml) under nitrogen. After 5 min., the solution was cooled to -78° and 15 min. later tert-butyl acetate (1.35 ml) was added over 5 min. After 20 min. cis-1,4-dichloro-2-butene (4 ml) was added and the mixture was allowed to warm to 10° over 4 h. The mixture was diluted with 1N HCl (25 ml) and extracted with ER (2×30 ml). The combined extracts were successively washed with 1N HCl (20 ml), brine (20 ml) and 8% NaHCO3 solution (20 ml) then dried and evaporated. The excess of dichloromethane was removed in vacuo and the residue was purified by chromatography (A) using PE, followed by 1:1 CH2Cl2 -PE increasing to CH2Cl2 as eluant to give the title compound as an oil (0.66 g)

1. additionwas added over 5 min
2. temperatureto warm to 10° over 4 h
3. extractionextracted with ER (2×30 ml)
4. washThe combined extracts were successively washed with 1N HCl (20 ml), brine (20 ml) and 8% NaHCO3 solution (20 ml)
5. customthen dried
6. customevaporated
7. customThe excess of dichloromethane was removed in vacuo
8. customthe residue was purified by chromatography (A)
9. temperatureincreasing to CH2Cl2 as eluant

ORD record

ord-bcdd4f58bd82420a8607fcd8c5afa1cb

Source dataset

uspto-grants-1989_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04880800