Sodium hydride → 6-Hydroxymethyl-4-(4-triisopropylsilanyloxybutyl)-4H-benzo[1,4]oxazin-3-one

HRID 1712606Notes

Reaction equation

HRID 1712606 reaction equation
[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[NH:8][C:7]=2[CH:13]=1.[H-].[Na+].Br[CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si:22]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:23]([CH3:25])[CH3:24].C(=O)([O-])O.[Na+]>CN(C)C=O>[OH:1][CH2:2][C:3]1[CH:4]=[CH:5][C:6]2[O:11][CH2:10][C:9](=[O:12])[N:8]([CH2:17][CH2:18][CH2:19][CH2:20][O:21][Si:22]([CH:26]([CH3:27])[CH3:28])([CH:23]([CH3:25])[CH3:24])[CH:29]([CH3:30])[CH3:31])[C:7]=2[CH:13]=1

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 184524436-(Hydroxymethyl)-2H-1,4-benzoxazin-3(4H)-oneHCID 86610030(4-Bromobutoxy)triisopropylsilane

Product 1

HCID 685022706-Hydroxymethyl-4-(4-triisopropylsilanyloxybutyl)-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The stirred solution of 3.70 g of 6-hydroxymethyl-4H-benzo[1,4]oxazin-3-one (Example 2d) and 95 ml of N,N-dimethylformamide is cooled to 0° C., admixed with 0.808 g of sodium hydride (60% dispersion) and stirred over 1 hour. After 7.57 g of (4-bromobutoxy)triisopropylsilane have been added, the mixture is stirred at 0° C. over a further 18 hours and the resulting reaction mixture is poured onto aqueous 1M sodium hydrogencarbonate solution (200 ml). The mixture is extracted with tert-butyl methyl ether (2×200 ml). The organic phases are washed successively with water (3×200 ml) and brine (200 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=0.43 (1:1 EtOAc-heptane); Rt=5.86.

Workup

  1. stirringthe mixture is stirred at 0° C. over a further 18 hours
  2. customthe resulting reaction mixture
  3. extractionThe mixture is extracted with tert-butyl methyl ether (2×200 ml)
  4. washThe organic phases are washed successively with water (3×200 ml) and brine (200 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-6034243ca1ab426592dd62cf235f3c51
Source dataset
uspto-grants-2010_09
Patent number
US07790715B2

Reaction notes

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