Ethyl bromoacetate → HCID 28932618, compound

HRID 1503627Notes

Reaction equation

HRID 1503627 reaction equation
[OH:1][C:2]1[C:9]([CH3:10])=[CH:8][C:5]([CH:6]=[O:7])=[CH:4][C:3]=1[CH3:11].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21]>CC(C)=O>[CH:6]([C:5]1[CH:4]=[C:3]([CH3:11])[C:2]([O:1][CH2:19][C:20]([O:22][CH2:23][CH3:24])=[O:21])=[C:9]([CH3:10])[CH:8]=1)=[O:7]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 752223,5-Dimethyl-4-hydroxybenzaldehyde

Product 1

HCID 28932618HCID 28932618, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

To a solution of 4-hydroxy-3,5-dimethylbenzaldehyde (500 mg, 3.33 mmol) in acetone (20 mL) was added cesium carbonate (1.41 g, 4.33 mmol), followed by ethyl bromoacetate (0.555 mL, 5 mmol). The mixture was refluxed in acetone under stirring for 1 hour. After evaporation of acetone under reduced pressure, 100 mL of water were added and the mixture was extracted with dichloromethane (200 mL). The organic phase was washed with brine (100 mL), dried over magnesium sulfate and concentrated under vacuum. The residue was purified by column chromatography over silica gel (eluent: dichloromethane) to give 580 mg of an oil (74% yield). 1H NMR (250 MHz, CDCl3): δ 1.25 (t, J=6.9 Hz, 3H), 4.27 (s, 6H), 4.21 (q, J=6.9 Hz, 2H), 4.38 (s, 2H), 7.44 (s, 2H), 9.77 (s, 1H). 13C NMR (126 MHz, CDCl3): δ 15.2, 17.4, 62.2, 70.1, 131.6, 132.8, 133.8, 161.7, 169.5, 192.1.

Workup

  1. customAfter evaporation of acetone under reduced pressure, 100 mL of water
  2. additionwere added
  3. extractionthe mixture was extracted with dichloromethane (200 mL)
  4. washThe organic phase was washed with brine (100 mL)
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under vacuum
  7. customThe residue was purified by column chromatography over silica gel (eluent: dichloromethane)

Sources & evidence

ORD record
ord-00465b573a644ad9968c55ee3663569d
Source dataset
uspto-grants-2015_12
Patent number
US09212196B2

Reaction notes

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