Potassium Carbonate → HCID 53820304, compound

HRID 2111980Notes

Reaction equation

HRID 2111980 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[CH:4][CH:3]=1.[CH3:18][O:19][C:20](=[O:29])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[CH2:27]Br.C([O-])([O-])=O.[K+].[K+]>C(#N)C>[C:13]([O:12][C:11]([NH:10][CH2:9][CH2:8][C:5]1[CH:4]=[CH:3][C:2]([O:1][CH2:27][C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[C:20]([O:19][CH3:18])=[O:29])=[CH:7][CH:6]=1)=[O:17])([CH3:14])([CH3:16])[CH3:15]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2734813Methyl 2-(bromomethyl)benzoateHCID 11831452tert-butyl N-(2-(4-hydroxyphenyl)ethyl)carbamate

Product 1

HCID 53820304HCID 53820304, compoundYield 94.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

tert-Butyl 2-(4-hydroxyphenyl)ethylcarbamate (3.534 g, 14.9 mmol), 2-bromomethyl-benzoic acid methyl ester (3.582 g, 15.6 mmol) and potassium carbonate, anhydrous (3.087 g, 22.3 mmol) were mixed in acetonitrile (50 ml). The mixture was heated to reflux overnight and then evaporated to dry. Water and ethyl acetate were added and the two phases were separated. The organic phase was dried (magnesium sulphate) and evaporated. Chromatography of the residue on a column (ISOLUTE® SI, 20 g/70 ml) using DCM and then MeOH/DCM (1:99) as eluant gave 5.427 g the desired product, yield 94.5%.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux overnight
  3. customevaporated
  4. customto dry
  5. additionWater and ethyl acetate were added
  6. customthe two phases were separated
  7. dry with materialThe organic phase was dried (magnesium sulphate)
  8. customevaporated

Sources & evidence

ORD record
ord-3ce0ba9d3355453a8524ec36c18fef84
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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