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

HRID 929472Notes

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

Participants

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

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

Sources & evidence

ORD record: ord-3290c16a22884a6591fc85989dc99e1a
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09296686B2

Reaction notes

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