Ethanol → HCID 86715429, compound

HRID 1503638Notes

Reaction equation

HRID 1503638 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[CH:5]=[O:6].C([O-])([O-])=O.[K+].[K+].[CH2:17]([O:19][C:20](=[O:23])[CH2:21]Br)[CH3:18].C(O)C>CC(C)=O>[CH:5]([C:4]1[CH:7]=[CH:8][C:9]([O:10][CH2:21][C:20]([O:19][CH2:17][CH3:18])=[O:23])=[C:2]([OH:1])[CH:3]=1)=[O:6]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 87683,4-DihydroxybenzaldehydeHCID 11430Potassium Carbonate

Product 1

HCID 86715429HCID 86715429, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 3,4 dihydroxybenzaldehyde (3.7 mmol) in dry acetone (20 ml), anhydrous K2CO3 (2.3 mmol), and ethylbromoacetate (3.4 mmol) at 0°. The mixture was stirred at room temperature for 20 h. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate The crude product was purified by silica gel chromatography (eluent dichloromethane). 112 mg of purified compound were obtained (15% yield). 1H NMR (250 MHz, CDCl3): δ 1.31 (t, J=7.1 Hz, 3H), 4.28 (q, J=7.1 Hz, 2H), 4.78 (q, J=6.8 Hz, 1H) 6.95 (d, J=8.8 Hz, 1H), 7.46 (d, J=8.9 Hz, 1H), 7.55 (s, 1H), 9.86 (s, 1H) 13C NMR (63 MHz, CDCl3): δ 15.2, 63.5, 67.1, 113.9, 117.1, 125.3, 132.8, 148.6, 152.4, 170.8, 193.3

Workup

  1. customThe compound was prepared
  2. customevaporated by azeotropic distillation with ethylbromoacetate The crude product
  3. customwas purified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-64bff31545aa49a28b2e383687952755
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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