Trimethyl orthoformate → 2-(1,1-Dimethoxyethyl)-3-phenylthiophene

HRID 507625Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 507625
[C:1]1([C:7]2[CH:8]=[C:9](C(=O)C)[S:10][CH:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH3:15][O:16][CH:17](OC)[O:18][CH3:19].O.[C:23]1(C)C=CC(S(O)(=O)=O)=CC=1>CO>[CH3:15][O:16][C:17]([C:11]1[S:10][CH:9]=[CH:8][C:7]=1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1)([O:18][CH3:19])[CH3:23]

Komponenten

5

Edukt 3

HCID 9005Trimethyl orthoformateHCID 521998p-Toluenesulfonic acid monohydrateHCID 135416931-(4-Phenylthiophen-2-yl)ethan-1-one

Produkt 1

HCID 574288492-(1,1-Dimethoxyethyl)-3-phenylthiophene

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

1-(4-Phenylthiophen-2-yl)ethanone (1.33 g, 6.57 mmol) was dissolved in MeOH and treated with trimethylorthoformate (1.44 mL, 13.2 mmol) and p-toluenesulfonic acid monohydrate (0.050 g). The resulting solution was stirred at ambient temperature for 16 h at which time the solution was partitioned between Et2O and saturated aqueous NaHCO3 solution. The organic phase was separated and washed with two portions of water and three portions of brine, then dried over Na2SO4 and concentrated in vacuo. The resulting white semi-solid was used without further purification. MS (M+H)+ 249.

Aufarbeitung

  1. customwas partitioned between Et2O and saturated aqueous NaHCO3 solution
  2. customThe organic phase was separated
  3. washwashed with two portions of water and three portions of brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting white semi-solid was used without further purification

Quellen und Nachweise

ORD-Eintrag
ord-d786b812e0c0479aa756995fdeadcd60
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07786132B2

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