Sodium hydride → Ethyl 4-benzyloxy-2-methyl-6-[3-(quinolin-2-ylmethoxy)-benzyloxy]-benzoate

HRID 892187Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:19]=[C:18]([CH3:20])[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:11]([OH:21])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Cl.Cl[CH2:26][C:27]1[CH:28]=[C:29]([CH:42]=[CH:43][CH:44]=1)[O:30][CH2:31][C:32]1[CH:41]=[CH:40][C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[N:33]=1>CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([O:21][CH2:26][C:27]2[CH:44]=[CH:43][CH:42]=[C:29]([O:30][CH2:31][C:32]3[CH:41]=[CH:40][C:39]4[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=4)[N:33]=3)[CH:28]=2)[C:12]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:18]([CH3:20])[CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of ethyl 4-benzyloxy-2-hydroxy-6-methyl-benzoate (5.1 g, 16 mmol, example 63) in DMF (100 mL), with 25° C. water bath cooling, is added 60% sodium hydride emulsion (1.3 g, 32 mmol) over 2 minutes. This mixture is stirred 30 minutes with the cooling bath removed. A solution of 3-(quinolin-2-ylmethoxy)-benzyl chloride hydrochloride (5.1 g, 16 mmol, example 49), in DMF (55 mL) is added and the reaction heated at 60° C. for 6 hours. The solvent is removed in vacuo and the residue purified by flash chromatography (silica, 0.5 to 2% methanol in dichloromethane) to give the title compound. MS (ESI) 534 (M+H)+.

Workup

customremoved
customThe solvent is removed in vacuo
customthe residue purified by flash chromatography (silica, 0.5 to 2% methanol in dichloromethane)

Sources & evidence

ORD record: ord-263c5128026d435e9464ec68fee1b2cf
Source dataset: uspto-grants-2006_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07005440B1

Reaction notes

Loading…