Thionyl Chloride → HCID 11740532, compound

HRID 1419632Notes

Reaction equation

HRID 1419632 reaction equation
[CH3:1][Si:2]([CH3:26])([C:22]([CH3:25])([CH3:24])[CH3:23])[O:3][C@H:4]1[CH2:9][C@H:8]([O:10][Si:11]([CH3:17])([CH3:16])[C:12]([CH3:15])([CH3:14])[CH3:13])[CH2:7][C:6]([C:19]#[CH:20])(O)[CH:5]1[CH3:21].S(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:26][Si:2]([CH3:1])([C:22]([CH3:25])([CH3:24])[CH3:23])[O:3][C@H:4]1[CH2:9][C@H:8]([O:10][Si:11]([CH3:16])([CH3:17])[C:12]([CH3:13])([CH3:14])[CH3:15])[CH2:7][C:6]([C:19]#[CH:20])=[C:5]1[CH3:21]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21308562HCID 21308562, compound

Product 1

HCID 11740532HCID 11740532, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

90 mg (0.23 mmol) of 10 in 8 ml of pyridine is introduced, and 50 μl of thionyl chloride is added under argon. It is stirred for 10 minutes at room temperature, poured onto ice water and extracted with ethyl acetate. The organic phase is washed with sodium bicarbonate solution and sodium chloride solution, dried on sodium sulfate, the solvent is removed and the crude product is purified by chromatography on silica gel (mobile solvent: EE:H=1:19; Rf =0.9), whereby 71 mg (0.20 mmol) of title compound 11 is obtained as a colorless oil.

Workup

  1. additionpoured onto ice water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase is washed with sodium bicarbonate solution and sodium chloride solution
  4. customdried on sodium sulfate
  5. customthe solvent is removed
  6. customthe crude product is purified by chromatography on silica gel (mobile solvent: EE:H=1:19; Rf =0.9)

Sources & evidence

ORD record
ord-674c772a613044d595e765deedfbd019
Source dataset
uspto-grants-1999_03
Patent number
US05886233

Reaction notes

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