(3-Bromopropyl)benzene → Ethyl-4-benzyloxy-2-methyl-6-(3-phenyl-propoxy)-benzoate

HRID 988242Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:21])[C:5]1[C:10]([CH3:11])=[CH:9][C:8]([O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:7][C:6]=1[OH:20])[CH3:2].[H-].[Na+].Br[CH2:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1>CN(C=O)C>[CH2:1]([O:3][C:4](=[O:21])[C:5]1[C:6]([O:20][CH2:25][CH2:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)=[CH:7][C:8]([O:12][CH2:13][C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:9][C:10]=1[CH3:11])[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl-4-benzyloxy-2-hydroxy-6-methyl-benzoate (0.5 g, 1.8 mmol) is dissolved in DMF (10 mL) and 60% sodium hydride (0.07 g, 1.8 mmol) is added and stirred 20 minutes, forming a clear solution. Then 1-bromo-3-phenyl propane (0.27 mL, 1.8 mol) is added and this mixture is heated at 100° C. for 4 hours and stirred at room temperature overnight. The solvent is removed in vacuo and the residue purified by flash chromatography (silica, 5% ethyl acetate in hexanes) to give the title compound: 1H NMR (300 MHz, CDCl3) δ 7.17-7.40 (m, 10H), 6.39 (d, 1H), 6.33 (d, 1H), 5.03 (s, 2H), 4.38 (q, 2H), 3.91 (t, 2H), 2.77 (t, 2H), 2.30 (s, 3H), 2.05 (m, 2H), 1.38 (t, 3H); MS (EI) 404 (M)+.

Workup

customforming a clear solution
stirringstirred at room temperature overnight
customThe solvent is removed in vacuo
customthe residue purified by flash chromatography (silica, 5% ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-7376c61c4dc247d79dd9197a9061f41d
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06635655B1

Reaction notes

Loading…