Ethanol → HCID 1020462, compound

HRID 1503630Notes

Reaction equation

HRID 1503630 reaction equation
[I:1][C:2]1[C:3]([OH:12])=[C:4]([O:10][CH3:11])[CH:5]=[C:6]([CH:9]=1)[CH:7]=[O:8].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>[I:1][C:2]1[CH:9]=[C:6]([CH:7]=[O:8])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[O:12][CH2:23][C:22]([O:21][CH2:19][CH3:20])=[O:25]

Participants

6

Reactant 4

HCID 702EthanolHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 79499Benzaldehyde, 4-hydroxy-3-iodo-5-methoxy-

Product 1

HCID 1020462HCID 1020462, compoundYield 49%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

The compound was prepared according to general procedure E with 5-iodovanillin (1.8 mmol) in dry acetone (25 ml), anhydrous K2CO3 (2.4 mmol), and ethylbromoacetate (2.7 mmol) at reflux for 1 h15. Ethanol was added and evaporated by azeotropic distillation with ethylbromoacetate. 673 mg of crude product were obtained and purified by silica gel chromatography (eluent dichloromethane). 320 mg of purified compound were obtained (49% yield). 1H NMR (250 MHz, CD3COCD3): δ 1.28 (t, J=7.2 Hz, 3H), 3.97 (s, 3H), 4.23 (q, J=7.2 Hz, 2H), 4.85 (s, 2H), 7.55 (s, 1H), 7.95 (s, 1H), 9.90 (s, 1H) 13C NMR (126 MHz, CD3COCD3): δ 15.2, 57.4, 62.1, 70.5, 92.4, 113.9, 135.1, 135.5, 153.1, 169.4, 191.1. MS (ESI): m/z 364.9 [M+H]+.

Workup

  1. customThe compound was prepared
  2. temperatureat reflux for 1 h15
  3. customevaporated by azeotropic distillation with ethylbromoacetate
  4. custom673 mg of crude product were obtained
  5. custompurified by silica gel chromatography (eluent dichloromethane)

Sources & evidence

ORD record
ord-4d206829d4fa4f65b0e8d95e5921b526
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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