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

HRID 929468
Notes
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Reaction equation

HRID 929468 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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
On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

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-eb26a58e5da44527ab9cfb776b1f08f3
Source dataset
uspto-grants-2016_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09296686B2

Reaction notes

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