Methyl Acrylate → HCID 53811637, compound

HRID 260992Notes

Reaction equation

HRID 260992 reaction equation
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.[C:16]([O:20][CH3:21])(=[O:19])[CH:17]=[CH2:18].C(N(CC)CC)C>CN(C=O)C>[CH2:9]([O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[CH:18]=[CH:17][C:16]([O:20][CH3:21])=[O:19])[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 7294Methyl AcrylateHCID 8471TriethylamineHCID 5618281-(Benzyloxy)-2-bromobenzene

Product 1

HCID 53811637HCID 53811637, compoundYield 55.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 2-bromo-O-benzyl phenol (J. Med. Chem. (1992) 35:3483) (2.17 g; 8.25 mmol), methyl acrylate (0.83 g; 9.9 mmol), dichloropalladium(II)bis(triphenylphosphine) (150 mg) and triethylamine (2.51 g; 24.7 mmol) in 10 mL of DMF was heated in a sealed tube to 120° C. for 16 hrs. After cooling, the tube's contents were partitioned between ethyl acetate and water. Removal of the organic solvent and purification on silica gel (20% ethyl acetate/hexane) afforded 1.22 g (55%) of methyl 2-benzoxycinnamate, 1H NMR (CDCl3): δ 3.78 (s, 3H); 5.15 (s, 2H); 6.54 (d, 1H, J=16.2); 6.95 (m, 2); 7.33-7.41 (m, 6H); 7.52 (d, 1H, J=7.7).

Workup

  1. temperatureAfter cooling
  2. customthe tube's contents were partitioned between ethyl acetate and water
  3. customRemoval of the organic solvent and purification on silica gel (20% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-bf936f0e12a84880884fe1c306eff87a
Source dataset
uspto-grants-1996_06
Patent number
US05530157

Reaction notes

Loading…