Trimethyl orthoformate → 61477-16-5

HRID 2196096Notes

Reaction equation

HRID 2196096 reaction equation
[S:1]1[CH2:6][CH2:5]C(=O)[CH2:3][CH2:2]1.[CH:8](OC)([O:11][CH3:12])[O:9][CH3:10]>CO.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C[O-].[Na+]>[CH3:10][O:9][C:8]1([O:11][CH3:12])[CH2:5][CH2:6][S:1][CH2:2][CH2:3]1

Participants

6

Reactant 2

HCID 9005Trimethyl orthoformateHCID 66173Tetrahydrothiopyran-4-one

Product 1

HCID 1233597761477-16-5Yield 99%

Reagents, catalysts & solvents 3

HCID 521998p-Toluenesulfonic acid monohydrateCatalystHCID 10942334Sodium MethoxideCatalystHCID 887MethanolSolvent

Procedure

A mixture of tetrahydro-(4H)-thiopyran-4-one (15.0 g, 129 mmol), trimethyl orthoformate (28.3 mL, 258 mmol) and para-toluenesulfonic acid monohydrate (67 mg, 0.35 mmol) in methanol (40 mL) was refluxed for 1 hour. The reaction mixture was cooled to room temperature, 1 M NaOMe (0.35 mL, 0.35 mmol) was added and excess methanol and trimethyl orthoformate was removed by distillation (atmospheric pressure). Further distillation under reduced pressure afforded 4,4-dimethoxytetrahydro-(4H)-thiopyran (20.7 g, 99%). 1H NMR (DMSO) δ 3.07 (s, 6H), 2.56 (m, 4H), 1.84 (m, 4H).

Workup

  1. temperaturewas refluxed for 1 hour
  2. customexcess methanol and trimethyl orthoformate was removed by distillation (atmospheric pressure)
  3. distillationFurther distillation under reduced pressure

Sources & evidence

ORD record
ord-92c8aa546e3d42708c76595a0d783aa3
Source dataset
uspto-grants-2012_12
Patent number
US08338431B2

Reaction notes

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