Chloroiodomethane → (S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone

Temperature

-78 °C

To a solution of (S)-methyl 2,2-dimethyl-1,3-dioxolane-4-carboxylate (1.3 g, 8.1 mmol) and chloroiodomethane (4.3 g, 24 mmol) in THF (50 mL) at −78° C. was added a solution of LDA (16.2 mL, 24 mmol) in portions over 10 minutes. The reaction was stirred at −78° C. for 10 minutes. To this mixture was added a 10% solution of acetic acid (50 mL) in THF at −78° C. After addition, the slurry was warmed to ambient temperature. The reaction was poured into EtOAc (200 mL) and the aqueous layer basified using 1 N NaOH. The organics were separated and washed with brine, dried over MgSO4 and concentrated in vacuo. The material was purified by chromatography using DCM as eluent to give (S)-2-chloro-1-(2,2-dimethyl-1,3-dioxolane-4-yl)ethanone (0.60 g, 3.4 mmol, 42% yield) as an oil.

1. additionAfter addition
2. temperaturethe slurry was warmed to ambient temperature
3. customThe organics were separated
4. washwashed with brine
5. dry with materialdried over MgSO4
6. concentrationconcentrated in vacuo
7. customThe material was purified by chromatography

ORD record

ord-b7c4027cdc354a2db8ea9cd6545bf4b5

Source dataset

uspto-grants-2014_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08853409B2