Sodium hydride → HCID 68500824, compound

HRID 1176534Notes

Reaction equation

HRID 1176534 reaction equation
[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[C:7]([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH:8]=[CH:9][CH:10]=2)[NH:5][C:4](=[O:20])[CH2:3]1.[H-].[Na+].Cl[CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30]>CN(C)C=O.O>[CH3:1][C:2]1([CH3:21])[C:11]2[C:6](=[C:7]([CH2:12][O:13][CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][O:15]3)[CH:8]=[CH:9][CH:10]=2)[N:5]([CH2:25][O:26][CH2:27][CH2:28][Si:29]([CH3:32])([CH3:31])[CH3:30])[C:4](=[O:20])[CH2:3]1

Participants

6

Reactant 3

HCID 24758Sodium hydride2×HCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl ether2×HCID 68499416HCID 68499416, compound

Product 1

HCID 68500824HCID 68500824, compound

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 6228DimethylformamideSolvent

Procedure

A solution of 1.4 g of 4,4-dimethyl-8-(tetrahydropyran-2-yloxymethyl)-3,4-dihydro-1H-quinolin-2-one in 10 ml of N,N-dimethylformamide is admixed at 0° C. with 0.2 g of sodium hydride dispersion (60%). After stirring for 1 hour, 0.94 ml of (2-chloromethoxyethyl)trimethylsilane are added and the reaction mixture is warmed to room temperature. After 17 hours and 22 hours, 0.1 g of sodium hydride dispersion (60%) and 0.5 ml of (2-chloromethoxyethyl)trimethylsilane are again added. After a total of 24 hours, the reaction mixture is admixed with a few drops of water and subsequently partitioned between tert-butyl methyl ether and saturated aqueous sodium bicarbonate solution. The organic phase is washed with water, dried over sodium sulphate and concentrated by evaporation. The title compound is obtained as a yellowish oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.37 (2:1 EtOAc-heptane); Rt=6.01.

Workup

  1. waitAfter 17 hours
  2. customAfter a total of 24 hours
  3. customsubsequently partitioned between tert-butyl methyl ether and saturated aqueous sodium bicarbonate solution
  4. washThe organic phase is washed with water
  5. dry with materialdried over sodium sulphate
  6. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-540ac964569b46f0a97ba90a46e38d6b
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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