Diethyl Ether → HCID 50913505, compound

HRID 929457Notes

Reaction equation

HRID 929457 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-042807c666514f069b1a1fd5a6d17c91
Source dataset
uspto-grants-2016_03
Patent number
US09296686B2

Reaction notes

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