Diethyl Ether → HCID 50914394, compound

HRID 335636Notes

Reaction equation

HRID 335636 reaction equation
[C:1]([Li])([CH3:4])([CH3:3])[CH3:2].[CH3:6][C:7]1([CH3:12])[O:11][CH2:10][CH2:9][O:8]1.[S:13]([Cl:16])(Cl)=[O:14].CC[O:19]CC>>[CH3:6][C:7]1([CH3:12])[O:11][C@@H:10]([CH2:2][C:1]2([S:13]([Cl:16])(=[O:14])=[O:19])[CH2:4][CH2:3]2)[CH2:9][O:8]1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 24386Thionyl ChlorideHCID 762092,2-Dimethyl-1,3-dioxolaneHCID 178418306HCID 178418306, compound

Product 1

HCID 50914394HCID 50914394, compound

Conditions

Temperature
-78 °C

Procedure

tert-Butyl lithium (2 eq) is added to a solution of (S)-4-(1-iodocyclopropyl)methyl)-2,2-dimethyl-1,3-dioxolane (1 eq) in ether at −78° C. and the mixture stirred at −78° C. for 30 mins. A solution of thionyl chloride in ether is added, the mixture warmed to room temperature and concentrated under reduced pressure. The residue is dissolved in chloroform, filtered and dried under reduced pressure.

Workup

  1. temperaturethe mixture warmed to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue is dissolved in chloroform
  4. filtrationfiltered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-c81a70f9346942a4811dc58b146a37a0
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Reaction notes

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