Sodium Hydroxide → HCID 51036575, compound

HRID 705469Notes

Reaction equation

HRID 705469 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](/[CH:9]=[CH:10]/[C:11](=[O:13])[CH3:12])=[CH:5][CH:4]=1.[OH-].[Na+].[F:16][C:17]([F:27])([F:26])[C:18]1[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=1>CO.O>[F:16][C:17]([F:26])([F:27])[C:18]1[CH:19]=[CH:20][C:21](/[CH:22]=[CH:12]/[C:11](=[O:13])/[CH:10]=[CH:9]/[C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[CH:24][CH:25]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 679964-(Trifluoromethyl)benzaldehydeHCID 736889(3E)-4-(4-Methoxyphenyl)-3-buten-2-one

Product 1

HCID 51036575HCID 51036575, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

(E)-4-(4-Methoxyphenyl)but-3-en-2-one (1 g, 5.7 mmol) was dissolved in MeOH (18 mL) and stirred for 5 min at room temperature. A solution of NaOH (500 mg, 12.5 mmol) in H2O (34 mL) was added and the reaction mixture was stirred for further 1 h. After the dropwise addition of 4-(trifluoromethyl)-benzaldehyde (822 μl, 6.0 mmol), the mixture was stirred overnight at ambient temperature. The resulting yellow precipitate was filtered and dried in vacuo to obtain NW336.2 as a pale yellow solid (1.75 g, 92%). mp: 144-146° C. 1H NMR (300 MHz, CDCl3) δ (ppm): 7.66 (d, 3J=15.9 Hz, 1H, Hvin), 7.64 (d, 3J=15.5 Hz, 1H, Hvin), 7.63 (d, 3J=9.0 Hz, 2H, HAr), 7.58 (d, 3J=8.6 Hz, 2H, HAr), 7.50 (d, 3J=8.8 Hz, 2H, HAr), 7.06 (d, 3J=16.0 Hz, 1H, Hvin), 6.87 (d, 3J=16.0 Hz, 1H, Hvin), 6.86 (d, 3J=8.8 Hz, 2H, HAr), 3.78 (s, 3H, OCH3). 13C NMR (75 MHz, CDCl3) δ (ppm): 188.4 (C), 161.9 (C), 143.9 (CH), 140.8 (CH), 138.4 (q, 4J(C, F)=1.3 Hz, CH), 131.7 (q, 2J(C, F)=32.7 Hz, C), 130.3 (CH), 128.4 (CH), 127.6 (CH), 127.3 (C), 125.9 (q, 3J(C, F)=3.8 Hz, CH), 123.9 (q, 1J(C, F)=272.2 Hz, C), 123.2 (CH), 114.5 (CH), 55.5 (OCH3). MS (FAB) m/z: 333.1 (M+). Anal. calcd for C19H15F3O2: C, 68.67; H, 4.55. Found: C, 68.81; H, 4.63%.

Workup

  1. stirringthe reaction mixture was stirred for further 1 h
  2. stirringthe mixture was stirred overnight at ambient temperature
  3. filtrationThe resulting yellow precipitate was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-829b4c8217914694aaed07ff99152e90
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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