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

HRID 335643Notes

Reaction equation

HRID 335643 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 86667891(S)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolaneHCID 178418306HCID 178418306, compound

Product 1

HCID 50914396(S)-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 (S)-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-d1e9741e79df487d872810d4131c4f87
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Reaction notes

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