Dimethylformamide dimethyl acetal → 3-Dimethylamino-2-(2-trifluoromethyl-benzoyl)-acrylic acid ethyl ester
Reaction equation
[CH2:1]([O:3][C:4](=[O:18])[CH2:5][C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:15])[F:14])[CH3:2].CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:18])[C:5]([C:6](=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[C:13]([F:16])([F:14])[F:15])=[CH:21][N:22]([CH3:24])[CH3:23])[CH3:2]Participants
Procedure
A solution of 3-oxo-3-(2-trifluoromethyl-phenyl)-propionic acid ethyl ester, prepared following an analogous procedure to that outlined in Example 231, (3.14 g, 12.1 mmol, 1.0 equiv) and 1,1-dimethoxy-N,N-dimethylmethanamine (5.60 mL, 42.2 mmol, 3.5 equiv) in N,N-dimethylformamide was heated to reflux for 5 hours. After cooling, the mixture was partitioned between ethyl acetate and water. The organic phase was separated and washed sequentially with water (4×) and saturated aqueous sodium chloride. The collected organic was dried over anhydrous sodium sulfate, filtered, and concentrated under vacuum to give 3.20 g (83%) of 3-dimethylamino-2-(2-trifluoromethyl-benzoyl)-acrylic acid ethyl ester as an orange waxy solid. 1H NMR (400 MHz, CDCl3) δ: 7.86 (s, 1H), 7.67-7.64 (m, 1H), 7.51-7.41 (m, 2H), 7.35 (d, 1H), 3.81 (q, 2H), 3.42-3.17 (m, 3H), 3.11-2.93 (m, 3H), 0.78-0.69 (t, 3H).
Workup
- temperaturewas heated
- temperatureto reflux for 5 hours
- temperatureAfter cooling
- customthe mixture was partitioned between ethyl acetate and water
- customThe organic phase was separated
- washwashed sequentially with water (4×) and saturated aqueous sodium chloride
- dry with materialThe collected organic was dried over anhydrous sodium sulfate
- filtrationfiltered
- concentrationconcentrated under vacuum
Sources & evidence
- ORD record
- ord-bc81539833954a33a13f33be454bbd23
- Source dataset
- uspto-grants-2014_01
- Patent number
- US08637526B2
Reaction notes
Loading…