Water → 2-(2-Benzyloxy-6-methoxy-phenyl)-5,5-dimethyl-3-(4-phenoxy-benzyl)-oxazolidin-4-one

HRID 2191607Notes

Reaction equation

[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[CH:17]1[NH:21][C:20](=[O:22])[C:19]([CH3:24])([CH3:23])[O:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].Br[CH2:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)=[CH:31][CH:30]=1.O>CN(C=O)C.CCCCCCC>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([O:15][CH3:16])[C:10]=1[CH:17]1[N:21]([CH2:28][C:29]2[CH:34]=[CH:33][C:32]([O:35][C:36]3[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=3)=[CH:31][CH:30]=2)[C:20](=[O:22])[C:19]([CH3:24])([CH3:23])[O:18]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a cold (0° C.) solution of 2-(2-benzyloxy-6-methoxy-phenyl)-5,5-dimethyl-oxazolidin-4-one (410 mg) in dry DMF (5 mL) is added portionwise NaH 90% (45 mg, 1.5 eq). The reaction mixture is stirred for 15 min at 0° C. and then commercially available 1-(bromomethyl)-4-phenoxybenzene (395 mg, 1.2 eq) is added and the reaction mixture is stirred at RT for 1 h. The reaction mixture is poured into water, extracted with DCM. The combined organic extracts are dried (MgSO4), filtered and concentrated to yield a crude oil. FC (EN n-heptane: 0/1 to 4/6) gives 2-(2-benzyloxy-6-methoxy-phenyl)-5,5-dimethyl-3-(4-phenoxy-benzyl)-oxazolidin-4-one as a colorless oil (0.495 g, 77%); LC-MS: tR=0.88 min; [M+H]+=510.33.

Workup

stirringthe reaction mixture is stirred at RT for 1 h
extractionextracted with DCM
dry with materialThe combined organic extracts are dried (MgSO4)
filtrationfiltered
concentrationconcentrated
customto yield a crude oil

Sources & evidence

ORD record: ord-a904b9763e72401fb5a3f4e9b459e6e9
Source dataset: uspto-grants-2012_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08329706B2

Reaction notes

Loading…