Ethanol → HCID 63320569, compound

HRID 1503635Notes

Reaction equation

HRID 1503635 reaction equation
[OH:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[C:10]([F:13])([F:12])[F:11].C([O-])([O-])=O.[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21].C(O)C>CC(C)=O>[CH:6]([C:5]1[CH:8]=[CH:9][C:2]([O:1][CH2:24][C:23]([O:22][CH2:20][CH3:21])=[O:26])=[C:3]([C:10]([F:11])([F:12])[F:13])[CH:4]=1)=[O:7]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 70215934-Hydroxy-3-(trifluoromethyl)benzaldehyde

Product 1

HCID 63320569HCID 63320569, compoundYield 59.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 4-hydroxy-3-(trifluoromethyl)benzaldehyde (1.3 mmol) in dry acetone (20 ml), anhydrous K2CO3 (1.7 mmol), and ethylbromoacetate (2.2 mmol) at reflux for 1 h. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. The crude product was purified by silica gel chromatography (eluent dichloromethane). 215 mg of purified compound were obtained (59% yield). 1H NMR (250 MHz, CDCl3): δ 1.30 (t, J=7.0 Hz, 3H), 4.28 (q, J=7.2 Hz, 2H), 4.85 (s, 2H), 7.02 (d, J=8.7 Hz, 1H), 8.04 (dd, J=8.9 and 2.0 Hz, 1H), 8.16 (d, J=2.0 Hz, 1H) 9.95 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 13.8, 61.6, 65.5, 112.9, 120.5 (d, J=32.0 Hz), 122.8 (d, J=273 Hz), 128.9, 129.6, 135.0, 160.1, 167.2, 189.6 MS (ESI): m/z 573.1 [2M+Na]+.

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. customThe crude product was purified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-87ed6975b12949f7b71dbbe322c7c97c
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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