Sodium Methoxide → HCID 86758335, compound

HRID 2228847Notes

Reaction equation

[CH3:1][O-].[Na+].[CH3:4][O:5][N:6]=[C:7]([CH2:12][C:13]([CH3:15])=[CH2:14])[C:8](=[N:10][OH:11])C.Br[CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=1[C:24](=[CH:29][O:30][CH3:31])[C:25]([O:27][CH3:28])=[O:26]>CN(C=O)C>[CH3:31][O:30][CH:29]=[C:24]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[CH:17]([O:11][N:10]=[CH:8][C:7](=[N:6][O:5][CH3:4])[CH2:12][C:13]([CH3:15])=[CH2:14])[CH3:1])[C:25]([O:27][CH3:28])=[O:26]

Participants

Conditions

Temperature: 23 °C

Procedure

112.2 g of a 30% strength methanolic solution of sodium methoxide were added to 11.5 g of 5-methylhex-5-ene-2,3-dione 3-(O-methyloxime) 2-oxime from Example 4 in 55 ml of DMF, and the mixture was stirred at 23° C. for 30 minutes. 21.3 g of methyl 2-(2-bromomethylphenyl)-3-methoxyacrylate (preparation: see U.S. Pat. No. 5,286,894) in 400 ml of DMF were subsequently added dropwise (temperature increase to up to 35° C.), and the reaction solution was stirred at 23° C. for one hour and then poured into ice-water/n-pentane. The mixture was subsequently stirred for one hour and the product was filtered off with suction, washed with water and a little n-pentane and dried under reduced pressure. Yield: 16.7 g of the title compound as a yellowish solid.

Workup

temperatureincrease to up to 35° C.), and the reaction solution
stirringwas stirred at 23° C. for one hour
stirringThe mixture was subsequently stirred for one hour
filtrationthe product was filtered off with suction
washwashed with water
dry with materiala little n-pentane and dried under reduced pressure

Sources & evidence

ORD record: ord-c6329c750855447d86cdf0ec44e0c44b
Source dataset: uspto-grants-2002_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06417388B1

Reaction notes

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