Diethyl Ether → (R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-ene-2-sulfonyl chloride

HRID 1895531Notes

Reaction equation

HRID 1895531 reaction equation
C([Li])(C)(C)C.I[C:7](=[CH2:16])[CH2:8][C@@H:9]1[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10]1.[S:17]([Cl:20])(Cl)=[O:18].CC[O:23]CC>>[CH3:14][C:11]1([CH3:15])[O:10][C@H:9]([CH2:8][C:7]([S:17]([Cl:20])(=[O:18])=[O:23])=[CH2:16])[CH2:13][O:12]1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 24386Thionyl ChlorideHCID 86667889(R)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolaneHCID 178418306HCID 178418306, compound

Product 1

HCID 50914395(R)-3-(2,2-dimethyl-1,3-dioxolan-4-yl)prop-1-ene-2-sulfonyl chloride

Conditions

Temperature
-78 °C

Procedure

tert-Butyl lithium is added to a solution of (R)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolane in ether at −78° C. and the mixture stirred at −78° C. for 30 mins. A solution of thionyl chloride in ether is then 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-f80e3ceb9fee4d2cb9c789a0542fa2c4
Source dataset
uspto-grants-2013_08
Patent number
US08513443B2

Reaction notes

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