Trimethyl orthoformate → 4,4-Dimethoxythiane

HRID 2196096Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2196096
[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

Komponenten

6

Edukt 2

HCID 9005Trimethyl orthoformateHCID 66173Tetrahydrothiopyran-4-one

Produkt 1

HCID 123359774,4-DimethoxythianeAusbeute 99 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 521998p-Toluenesulfonic acid monohydrateKatalysatorHCID 10942334Sodium MethoxideKatalysatorHCID 887MethanolLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-92c8aa546e3d42708c76595a0d783aa3
Quelldatensatz
uspto-grants-2012_12
Patentnummer
US08338431B2

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