Ethanol → HCID 86715426, compound

HRID 1503631Notes

Reaction equation

HRID 1503631 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].[CH2:19]([O:21][C:22](=[O:25])[CH2:23]Br)[CH3:20].C(O)C>CC(C)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:5]=[O:6])[CH:7]=[C:8]([O:11][CH3:12])[C:9]=1[O:10][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 5984523-Fluoro-4-hydroxy-5-methoxybenzaldehyde

Product 1

HCID 86715426HCID 86715426, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 3-fluoro-4-hydroxy-5-methoxybenzaldehyde (1.8 mmol) in dry acetone (20 ml), anhydrous K2CO3 (2.4 mmol), and ethylbromoacetate (2.7 mmol) at reflux for 1 h. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 395 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 361 mg of purified compound were obtained (79% yield). 1H NMR (500 MHz, CD3COCD3): δ 1.25 (t, J=, 3H), 3.98 (s, 3H), 4.21 (q, J=, 2H), 4.89 (s, 2H), 7.34 (dd, J=10.3 and 1.6 Hz, 1H), 7.40 (t, J=1.6 Hz, 1H), 9.88 (d, J=1.6 Hz, 1H) 13C NMR (126 MHz, CD3COCD3): δ 15.0, 57.6, 62.1, 70.3, 110.0, 111.8 (d, J=20.6 Hz), 133.1 (d, J=7.2 Hz), 141.8 (d, J=12.7 Hz), 154.5 (d, J=4.5 Hz), 156.0 (d, J=246 Hz), 169.7, 191.3. MS (ESI): m/z 256.9 [M+H]+.

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom395 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-578a55d64c28463a824a698f5ac1319e
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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