Benzyl Bromide → 5-((3-Benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione

HRID 393595Notes

Reaction equation

[OH:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH:5][CH:6]=[C:7]1[C:12](=[O:13])[O:11][C:10]([CH3:15])([CH3:14])[O:9][C:8]1=[O:16].C(=O)([O-])[O-].[K+].[K+].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CN(C=O)C>[CH2:28]([O:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][C:19]=1[O:20][CH3:21])[NH:5][CH:6]=[C:7]1[C:12](=[O:13])[O:11][C:10]([CH3:14])([CH3:15])[O:9][C:8]1=[O:16])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

Conditions

Temperature: 65 °C

Procedure

A mixture of 5-((3-hydroxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (20 g, 69 mmol), potassium carbonate (12.4 g, 90 mmol) and benzyl bromide (15.4 g, 90 mmol) in DMF (100 ml) was heated at 65° C. for 2 hours. Two thirds of the DMF was removed from the mixture by evaporation, the mixture was diluted with water, adjusted to pH4 with 5M hydrochloric acid and extracted with ethyl acetate. The combined extracts were washed with water and then brine, dried (MgSO4) and the volatiles removed by evaporation. The solid residue was triturated with ether, and collected by filtration and dried under vacuum to give 5-((3-benzyloxy-4-methoxyanilino)methylene)-2,2-dimethyl-1,3-dioxane-4,6-dione (22 g, 83%) as a cream solid.

Workup

customTwo thirds of the DMF was removed from the mixture by evaporation
additionthe mixture was diluted with water
extractionextracted with ethyl acetate
washThe combined extracts were washed with water
dry with materialbrine, dried (MgSO4)
customthe volatiles removed by evaporation
customThe solid residue was triturated with ether
filtrationcollected by filtration
customdried under vacuum

Sources & evidence

ORD record: ord-ca3bb5cda7084d30afd871c908917915
Source dataset: uspto-grants-2004_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06809097B1

Reaction notes

Loading…