1-Bromo-2-butanone → HCID 135974501, compound

HRID 603435Notes

Reaction equation

HRID 603435 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][C:3]=1[O:11][CH3:12].Br[CH2:14][C:15](=O)[CH2:16][CH3:17]>C1(C)C=CC=CC=1.O1CCOCC1>[CH2:16]([C:15]1[N:8]=[C:6]([C:5]2[CH:9]=[CH:10][C:2]([OH:1])=[C:3]([O:11][CH3:12])[CH:4]=2)[O:7][CH:14]=1)[CH3:17]

Participants

5

Reactant 2

HCID 131561-Bromo-2-butanoneHCID 354088Vanillamide

Product 1

HCID 135974501HCID 135974501, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
125 °C

Procedure

To a solution of the amide prepared in Example 171 (460 mg, 2.75 mmol) in toluene (3 mL) and 1,4-dioxane (3 mL) was added 1-bromo-2-butanone (623 mg, 4.13 mmol), and the solution was heated to 125° C. for 18 h. The reaction mixture was cooled to rt, and then concentrated under reduced pressure. Purification by silica gel chromatography (EtOAc:hexane (v/v)=4:1) gave 382 mg (73%) of the title compound as a yellow oil. 1H NMR (400 MHz, DMSO-d6): δ 9.60 (s, 1H), 7.78 (s, 1H), 7.39 (d, 1H), 7.36 (dd, 1H), 6.83 (d, 1H), 3.79 (s, 3H), 2.45 (m, 2H), 1.18 (t, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to rt
  2. concentrationconcentrated under reduced pressure
  3. customPurification by silica gel chromatography (EtOAc:hexane (v/v)=4:1)

Sources & evidence

ORD record
ord-c6d60af0d0c343cbbb1d840861b9ae18
Source dataset
uspto-grants-2011_03
Patent number
US07906653B2

Reaction notes

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