Thionyl Chloride → methyl 4-(2-chloro-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate

HRID 907674Notes

Reaction equation

HRID 907674 reaction equation
[CH3:1][O:2][C:3]([C:5]1([CH2:11][C:12]([OH:14])=O)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1)=[O:4].S(Cl)([Cl:17])=O>>[Cl:17][C:12](=[O:14])[CH2:11][C:5]1([C:3]([O:2][CH3:1])=[O:4])[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 219856952-[4-(Methoxycarbonyl)oxan-4-yl]acetic acid

Product 1

HCID 21985713methyl 4-(2-chloro-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylateYield 99%

Procedure

Thionyl chloride (20 mL) was added to [4-(methoxycarbonyl)tetrahydro-2H-pyran-4-yl]acetic acid (970 mg, 4.80 mmol) and the solution was stirred at rt for 3 h. The solvent was then removed and mixture was azeotroped with dichloroethane three times to afford methyl 4-(2-chloro-2-oxoethyl)tetrahydro-2H-pyran-4-carboxylate (1.05 g, 99%), which was used without purification in the next step.

Workup

  1. customThe solvent was then removed
  2. custommixture was azeotroped with dichloroethane three times

Sources & evidence

ORD record
ord-69bd55f38be945cf849c61d5598fd489
Source dataset
uspto-grants-2011_09
Patent number
US08013166B2

Reaction notes

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