Sodium t-butoxide → 1-(3-Methoxypropyl)-3,3,6-trimethyl-1,3-dihydroindol-2-one

HRID 1176308Notes

Reaction equation

CC(C)([O-])C.[Na+].Br[C:8]1[CH:13]=[CH:12][C:11]([CH3:14])=[CH:10][C:9]=1[N:15]([CH2:21][CH2:22][CH2:23][O:24][CH3:25])[C:16](=[O:20])[CH:17]([CH3:19])[CH3:18]>O1CCOCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:25][O:24][CH2:23][CH2:22][CH2:21][N:15]1[C:9]2[C:8](=[CH:13][CH:12]=[C:11]([CH3:14])[CH:10]=2)[C:17]([CH3:19])([CH3:18])[C:16]1=[O:20]

Participants

Conditions

Temperature: 50 °C

Procedure

The solution, prepared under argon, of 0.226 g of 1,3-bis(2,6-Di-L-propylphenyl)imidazolium chloride, 0.116 g of palladium(II) acetate and 1.497 g of sodium tert-butoxide in 90 ml of dioxane is admixed with stirring with the solution of 3.34 g of N-(2-bromo-5-methylphenyl)-N-(3-methoxypropyl)isobutyramide in 10 ml of dioxane and stirred at 50° C. over 22 hours. The reaction mixture is cooled, poured onto ice-water (250 ml) and extracted with tert-butyl methyl ether (2×250 ml). The organic phases are washed successively with water (2×250 ml) and brine (1×250 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a slightly yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.26 (1:1 EtOAc-heptane); Rt=16.60 (II).

Workup

temperatureThe reaction mixture is cooled
additionpoured onto ice-water (250 ml)
extractionextracted with tert-butyl methyl ether (2×250 ml)
washThe organic phases are washed successively with water (2×250 ml) and brine (1×250 ml)
dry with materialdried over sodium sulphate
filtrationfiltered
concentrationconcentrated by evaporation

Sources & evidence

ORD record: ord-fef38e49701a4f68b87d5e0dbc45e1e6
Source dataset: uspto-grants-2010_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07842688B2

Reaction notes

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