Thionyl Chloride → (Tetrahydro-2H-pyran-4-yl)acetyl chloride

HRID 2353504Notes

Reaction equation

HRID 2353504 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([OH:10])=O)[CH2:3][CH2:2]1.S(Cl)([Cl:13])=O>>[O:1]1[CH2:6][CH2:5][CH:4]([CH2:7][C:8]([Cl:13])=[O:10])[CH2:3][CH2:2]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 2773575Tetrahydropyran-4-ylacetic acid

Product 1

HCID 24229747(Tetrahydro-2H-pyran-4-yl)acetyl chloride

Procedure

A solution of tetrahydropyran-4-yl acetic acid (Combi-Blocks, Inc., 0.18 g, 1.2 mmol) in thionyl chloride (7 mL, 96 mmol, excess) was refluxed for 1 h then was cooled to ambient temperature and concentrated under reduced pressure. The residue was azeotroped twice with 10 mL of benzene to remove any remaining thionyl chloride. The resulting acid chloride was used without further purification.

Workup

  1. concentrationconcentrated under reduced pressure
  2. customThe residue was azeotroped twice with 10 mL of benzene
  3. customto remove any remaining thionyl chloride
  4. customThe resulting acid chloride was used without further purification

Sources & evidence

ORD record
ord-b21d60aeb6c3473c82bcd6c8759c3b2d
Source dataset
uspto-grants-2010_07
Patent number
US07750039B2

Reaction notes

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