2-Propionylthiophene → 3-(Dimethylamino)-2-methyl-1-(2-thienyl)-2-propen-1-one

HRID 507648Notes

Reaction equation

HRID 507648 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:9])[CH2:7][CH3:8].C(O[CH:15]([N:19]([CH3:21])[CH3:20])N(C)C)(C)(C)C>>[CH3:21][N:19]([CH3:20])[CH:15]=[C:7]([CH3:8])[C:6]([C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)=[O:9]

Participants

3

Reactant 2

HCID 261792-PropionylthiopheneHCID 79885tert-Butoxy bis(dimethylamino)methane

Product 1

HCID 684666763-(Dimethylamino)-2-methyl-1-(2-thienyl)-2-propen-1-one

Conditions

Temperature
55 °C

Procedure

1-(Thiophen-2-yl)propan-1-one (0.15 g, 1.069 mmol) was treated with tert-butoxybis-(dimethylamino)methane (0.5 mL) and the mixture stirred at 55° C. overnight. The volatiles were removed in vacuo and the residual liquid was azeotroped with toluene. The resulting residue was dissolved in ethyl acetate and passed through a plug of silica gel. The filtrate was concentrated and placed under vacuum to afford a thick yellow oil. Yield=0.2 g. MS (M+H)+ 196.

Workup

  1. customThe volatiles were removed in vacuo
  2. customthe residual liquid was azeotroped with toluene
  3. dissolutionThe resulting residue was dissolved in ethyl acetate
  4. concentrationThe filtrate was concentrated
  5. customto afford a thick yellow oil

Sources & evidence

ORD record
ord-2d1adb23ef954147b653012e5202b84c
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

Loading…