Acetone → HCID 89188746, compound

HRID 1503639Notes

Reaction equation

HRID 1503639 reaction equation
[CH:1](=[O:13])[C:2]1[CH:12]=[C:9](OC)[C:7]([OH:8])=[C:4](OC)[CH:3]=1.[C:14]([O-:17])([O-:16])=O.[K+].[K+].[CH2:20]([O:22][C:23](=[O:26])[CH2:24]Br)[CH3:21].[CH2:27]([OH:29])[CH3:28].[CH3:30][C:31](C)=[O:32]>>[CH2:20]([O:22][C:23](=[O:26])[CH2:24][O:8][C:7]1[CH:4]=[CH:3][C:2]([CH:1]=[O:13])=[CH:12][C:9]=1[C:14]([O:17][CH2:28][C:27]([O:32][CH2:31][CH3:30])=[O:29])=[O:16])[CH3:21]

Participants

6

Reactant 5

HCID 180AcetoneHCID 702EthanolHCID 7748Ethyl bromoacetateHCID 8655SyringaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 89188746HCID 89188746, compoundYield 31%

Procedure

The compound was prepared according to general procedure E with syringaldehyde (2.1 mmol) in dry acetone (10 ml), anhydrous K2CO3 (2.7 mmol), and ethylbromoacetate (2.5 mmol) at reflux for 4 h. Ethanol was added and evaporated by azeotropic distillation with Ethylbromoacetate. The crude product was purified by silica gel chromatography (eluent dichloromethane). 221 mg of purified compound were obtained (31% yield). 1H NMR (250 MHz, CDCl3): δ 1.30 (t, J=7.2 Hz, 3H), 4.24 (q, J=7.4 Hz, 2H), 4.81 (s, 2H), 4.84 (s, 2H), 6.98 (d, J=8.7 Hz, 1H), 8.0 (dd, J=8.9 and 1.9 Hz, 1H), 8.44 (d, J=1.9 Hz, 1H), 9.91 (s, 1H) 13C NMR (126 MHz, CDCl3): δ 15.3, 62.7, 67.2, 115.0, 121.3, 131.2, 135.9, 135.9 (2C), 163.3, 165.0, 168.9, 191.2

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 4 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-5244b12b5f5e4b85a7de601289cd2060
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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