p-Toluenesulfonic acid monohydrate → 3,3-Dimethoxythiane-2-carboxylic acid ethyl ester

HRID 483111Notes

Reaction equation

HRID 483111 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[C:11](=[O:12])[CH2:10][CH2:9][CH2:8][S:7]1)=[O:5])[CH3:2].[CH:13]([O-])([O-])[O:14]C.O.[C:19]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH2:1]([O:3][C:4]([CH:6]1[C:11]([O:14][CH3:13])([O:12][CH3:19])[CH2:10][CH2:9][CH2:8][S:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 12269128ethyl 3-oxotetrahydro-2H-thiopyran-2-carboxylateHCID 53629101Methylorthoformate

Product 1

HCID 541841023,3-Dimethoxythiane-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixture of 3-oxothiane-2-carboxylic acid ethyl ester (2.0 g), methanol (8 ml), and methyl orthoformate (20 ml) is added p-toluenesulfonic acid monohydrate (120 mg). After refluxing overnight, the mixture is concentrated, diluted with ethyl acetate, washed with water, dried, and concentrated to give 3,3-dimethoxythiane-2-carboxylic acid ethyl ester (1.32 g).

Workup

  1. temperatureAfter refluxing overnight
  2. concentrationthe mixture is concentrated
  3. additiondiluted with ethyl acetate
  4. washwashed with water
  5. customdried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-20d8115fdcc24caab29ad2475c01bf02
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Reaction notes

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