Diethyl Ether → HCID 50913505, compound

HRID 335629Notes

Reaction equation

HRID 335629 reaction equation
C([Li])(C)(C)C.I[C:7]1([CH2:10][C@@H:11]2[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]2)[CH2:9][CH2:8]1.[S:18]([Cl:21])(Cl)=[O:19].CC[O:24]CC>>[CH3:16][C:13]1([CH3:17])[O:12][C@H:11]([CH2:10][C:7]2([S:18]([Cl:21])(=[O:19])=[O:24])[CH2:9][CH2:8]2)[CH2:15][O:14]1

Participants

5

Reactant 4

HCID 3283Diethyl Ether2×HCID 24386Thionyl ChlorideHCID 66849068HCID 66849068, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 50913505HCID 50913505, compoundYield 57%

Conditions

Temperature
-78 °C

Procedure

tert-Butyl lithium (0.2 mL, 0.34 mmol, 1.7M) was added to a solution of (R)-4-(1-iodocyclopropyl)methyl)-2,2-dimethyl-1,3-dioxolane (step G, 45 mg, 0.16 mmol) in ether (1 mL) at −78° C. and the mixture stirred at −78° C. for 30 mins. A solution of thionyl chloride (26 μL) in ether (0.5 mL) was then added. The resulting orange solution was warmed to room temperature and concentrated under reduced pressure. The residue was dissolved in chloroform, filtered and dried under reduced pressure to afford (R)-1-((2,2-dimethyl-1,3-dioxolan-4-yl)methyl)cyclopropane-1-sulfonyl chloride (23.7 mg, 57%).

Workup

  1. temperatureThe resulting orange solution was warmed to room temperature
  2. concentrationconcentrated under reduced pressure
  3. dissolutionThe residue was dissolved in chloroform
  4. filtrationfiltered
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-0faa82dda33a48ca8adcfaf4b06ca5e0
Source dataset
uspto-grants-2014_11
Patent number
US08884058B2

Reaction notes

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