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

HRID 335644
Notes
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Reaction equation

HRID 335644 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)([Cl:20])(=[O:19])=[O:18]>CCCCCC.C(OCC)C>[CH3:14][C:11]1([CH3:15])[O:10][C@H:9]([CH2:8][C:7]([S:17]([Cl:20])(=[O:19])=[O:18])=[CH2:16])[CH2:13][O:12]1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24648Sulfuryl 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

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent
HCID 8058
Hexane
Solvent

Conditions

Temperature
-78 °C

Procedure

A solution of tert-butyl lithium in hexane (1.7M, 7.65 mL) was added dropwise to a solution of (R)-4-(2-iodoallyl)-2,2-dimethyl-1,3-dioxolane (1.21, 6.5 mmol) in diethyl ether (12 mL) at −78° C., and the reaction stirred at −78° C. for 30 min. Sulfuryl dichloride (SO2Cl2, 538 μL, 6.5 mmol) was added, the mixture warmed to room temperature and the solvents removed under reduced pressure. The product was used in the next step with no further purification.

Workup

  1. temperaturethe mixture warmed to room temperature
  2. customthe solvents removed under reduced pressure
  3. customThe product was used in the next step with no further purification

Sources & evidence

ORD record
ord-83adb21d82b2466f87b39ef6748c0f1f
Source dataset
uspto-grants-2014_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08884058B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes