Potassium Carbonate → HCID 131729541, compound

HRID 1686151Notes

Reaction equation

HRID 1686151 reaction equation
[Br:1][C:2]1[CH:18]=[CH:17][CH:16]=[CH:15][C:3]=1[CH2:4][O:5][C:6]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:7]=1[CH:8]=[O:9].[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][CH2:27]Br)([CH3:22])([CH3:21])[CH3:20].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:19]([O:23][C:24](=[O:29])[NH:25][CH2:26][CH2:27][O:14][C:12]1[CH:11]=[CH:10][C:7]([CH:8]=[O:9])=[C:6]([O:5][CH2:4][C:3]2[CH:15]=[CH:16][CH:17]=[CH:18][C:2]=2[Br:1])[CH:13]=1)([CH3:22])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 4103526tert-Butyl N-(2-bromoethyl)carbamateHCID 86627410HCID 86627410, compound

Product 1

HCID 131729541HCID 131729541, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 2-(2-bromobenzyloxy)-4-hydroxybenzaldehyde (60 mg, 020 mmol) in DMF (10 ml) were added t-butyl-2-bromoethylcarbamate (43.70 g, 0.20 mmol) and K2CO3 (54.18 mg, 0.39 mmol), followed by stirring at 100° C. for 3 hours. After completion of the reaction, the solution was extracted with a saturated aqueous NH4Cl solution and ethyl acetate. The organic layer was dried over anhydrous MgSO4 and filtered. The filtrate was concentrated in a vacuum. The residue was purified through column chromatography (ethyl acetate/n-hexane=1/9→1/5) to afford the object compound (pale yellowish solid, 69 mg, 79.3%).

Workup

  1. customAfter completion of the reaction
  2. extractionthe solution was extracted with a saturated aqueous NH4Cl solution and ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous MgSO4
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated in a vacuum
  6. customThe residue was purified through column chromatography (ethyl acetate/n-hexane=1/9→1/5)
  7. customto afford the object compound (pale yellowish solid, 69 mg, 79.3%)

Sources & evidence

ORD record
ord-6af61eb30be6466487b763aa9384dcb5
Source dataset
uspto-grants-2012_04
Patent number
US08148541B2

Reaction notes

Loading…