3-Nitrobenzaldehyde → 6-Methoxy-2,2-dimethyl-3-(3-nitrobenzylidene)chroman-4-one

HRID 1684626Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:14])([CH3:13])[CH2:7][C:6]2=[O:15].[Si](OC)(OC)(OC)OC.[F-].[K+].[N+:27]([C:30]1[CH:31]=[C:32]([CH:35]=[CH:36][CH:37]=1)[CH:33]=O)([O-:29])=[O:28]>CN(C)C=O.CCOCC.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[O:9][C:8]([CH3:13])([CH3:14])[C:7](=[CH:33][C:32]1[CH:35]=[CH:36][CH:37]=[C:30]([N+:27]([O-:29])=[O:28])[CH:31]=1)[C:6]2=[O:15]

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 7.0 g (0.034 mole) of the product of Example 109, 2.5 mL (2.6 g, 0.017 mole) tetramethyl orthosilicate, 1.9 g (0.034 mole) potassium fluoride and 5.1 g (0.034 mole) 3-nitrobenzaldehyde in 10 mL dimethylformamide was heated to 80° C. for 4 hours. The mixture was diluted with ether and washed successively with 1N HCl, 5% NaHCO3, water and brine and then dried (MgSO4) and concentrated to give an oil. Flash chromatography on silica gel eluting with 20% ethyl acetate in hexanes yielded an oil. Recrystallization from ether/hexanes afforded 6.9 g (60%) of the title product as a solid. Mp 103°-105° C. Analysis calculated for C15H17NO5 : C, 67.25; H, 5.05; N, 4.13. Found: C, 67.22; H, 4.87; N, 4.11.

Workup

washwashed successively with 1N HCl, 5% NaHCO3, water and brine
dry with materialdried (MgSO4)
concentrationconcentrated
customto give an oil
customRecrystallization from ether/hexanes

Sources & evidence

ORD record: ord-50a5bad39c834ba4bbdcd4cbed2b71dc
Source dataset: uspto-grants-1997_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05641789

Reaction notes

Loading…