Thionyl Chloride → 2-(Cyclopentyloxy)acetyl chloride

HRID 1912937Notes

Reaction equation

HRID 1912937 reaction equation
[CH:1]1([O:6][CH2:7][C:8]([OH:10])=O)[CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:13])=O>>[CH:1]1([O:6][CH2:7][C:8]([Cl:13])=[O:10])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 13355021(Cyclopentyloxy)acetic acid

Product 1

HCID 866419172-(Cyclopentyloxy)acetyl chloride

Conditions

Temperature
70 °C

Procedure

The product from Example 133B (0.33 g, 2.29 mmol) was taken up in thionyl chloride (4 mL, 54.8 mmol) and heated at 70° C. for 1 hour. The reaction mixture was cooled to room temperature and concentrated under vacuum. The residue was taken up in CH2Cl2 (5 mL) and concentrated again to remove excess thionyl chloride. This was repeated twice more. The residue was dissolved in CH2Cl2 (2.5 mL) to provide a solution of the title compound that was used for the next step.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. concentrationconcentrated under vacuum
  3. concentrationconcentrated again
  4. customto remove excess thionyl chloride
  5. dissolutionThe residue was dissolved in CH2Cl2 (2.5 mL)

Sources & evidence

ORD record
ord-f2c73572575545ae86f19667850ac038
Source dataset
uspto-grants-2013_12
Patent number
US08609669B2

Reaction notes

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