Potassium Carbonate → HCID 68181978, compound

HRID 705472Notes

Reaction equation

HRID 705472 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:12])[CH3:11])=[CH:4][C:3]=1[O:13][CH3:14].C([O-])([O-])=O.[K+].[K+].[F:21][C:22]([F:33])([F:32])[O:23][C:24]1[CH:31]=[CH:30][C:27]([CH:28]=O)=[CH:26][CH:25]=1>CCO.O>[OH:1][C:2]1[CH:7]=[CH:6][C:5](/[CH:8]=[CH:9]/[C:10](=[O:12])/[CH:11]=[CH:28]/[C:27]2[CH:30]=[CH:31][C:24]([O:23][C:22]([F:21])([F:32])[F:33])=[CH:25][CH:26]=2)=[CH:4][C:3]=1[O:13][CH3:14]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 69573p-(Trifluoromethoxy)benzaldehydeHCID 5354238(3E)-4-(4-Hydroxy-3-methoxyphenyl)-3-buten-2-one

Product 1

HCID 68181978HCID 68181978, compoundYield 17%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of (E)-4-(4-hydroxy-3-methoxyphenyl)but-3-en-2-one (600 mg, 3.1 mmol) in EtOH (10 mL) was stirred for 5 min at 0° C. A solution of K2CO3 (863 mg, 6.2 mmol) in H2O (5 mL) was added and the reaction mixture was stirred for further 10 min at 0° C. After the dropwise addition of 4-(trifluoromethoxy)-benzaldehyde (473 μl, 3.3 mmol), the orange suspension was heated to reflux for 4 d at 40° C. The solvent was evaporated in vacuo and the resulting residue was purified by flash-chromatography on silica gel (Hexane/EtOAc 2:1) and dried in vacuo to obtain NW351 as a yellow solid (191 mg, 17%). mp: 93-95° C. 1H NMR (300 MHz, CD3OD) δ (ppm): 7.72 (d, 3J=8.4 Hz, 2H, HAr), 7.71 (d, 3J=15.9 Hz, 1H, Hvin), 7.68 (d, 3J=15.6 Hz, 1H, Hvin), 7.27 (d, 3J=8.3 Hz, 2H, HAr), 7.24 (d, 4J=1.9 Hz, 1H, HAr), 7.19 (d, 3J=16.0 Hz, 1H, Hvin), 7.15 (dd, 3J=8.4 Hz, 4J=2.0 Hz, 1H, HAr), 7.02 (dd, 3J=15.9 Hz, 5J=0.99, Hz, 1H, Hvin), 6.83 (dd, 3J=8.2 Hz, 5J=0.9 Hz, 1H, HAr), 3.89 (d, 5J=0.9, 3H, OCH3). 13C NMR (75 MHz, CD3OD) δ (ppm): 191.1 (C), 151.7 (q, 4J (C, F)=1.7 Hz), 151.2 (C), 149.4 (C), 146.4 (CH), 142.4 (CH), 135.4 (C), 131.3 (CH), 128.1 (C), 127.6 (CH), 125.0 (CH), 123.6 (CH), 122.3 (CH), 120.2 (C), 116.7 (CH), 112.2 (CH), 56.5 (OCH3). MS (FAB) m/z: 365.2 (M+). Anal. calcd for C19H15F3O4: C, 62.64; H, 4.15. Found: C, 62.45; H, 4.39%.

Workup

  1. stirringthe reaction mixture was stirred for further 10 min at 0° C
  2. temperaturethe orange suspension was heated
  3. temperatureto reflux for 4 d at 40° C
  4. customThe solvent was evaporated in vacuo
  5. customthe resulting residue was purified by flash-chromatography on silica gel (Hexane/EtOAc 2:1)
  6. customdried in vacuo

Sources & evidence

ORD record
ord-85e02bff8f344a699340ab39073c87ab
Source dataset
uspto-grants-2015_11
Patent number
US09174960B2

Reaction notes

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