Sodium hydride → 6-(tetrahydropyran-2-yloxymethyl)-4-(2-triisopropylsilanyloxyethyl)-4H-benzo[1,4]oxazin-3-one

HRID 1176508Notes

Reaction equation

HRID 1176508 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15](=[O:18])[NH:14][C:13]=2[CH:19]=1.[H-].[Na+].I[CH2:23][CH2:24][O:25][Si:26]([CH:33]([CH3:35])[CH3:34])([CH:30]([CH3:32])[CH3:31])[CH:27]([CH3:29])[CH3:28]>CN(C)C=O.O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]1[CH:10]=[CH:11][C:12]2[O:17][CH2:16][C:15](=[O:18])[N:14]([CH2:23][CH2:24][O:25][Si:26]([CH:30]([CH3:31])[CH3:32])([CH:27]([CH3:29])[CH3:28])[CH:33]([CH3:34])[CH3:35])[C:13]=2[CH:19]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 11450272(2-Iodoethoxy)triisopropylsilaneHCID 685039936-(Tetrahydropyran-2-yloxymethyl)-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 685000956-(tetrahydropyran-2-yloxymethyl)-4-(2-triisopropylsilanyloxyethyl)-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 21974620tetrahydrofuran N,N-dimethylformamideSolvent

Procedure

The solution of 5.50 g of 6-(tetrahydropyran-2-yloxymethyl)-4H-benzo[1,4]oxazin-3-one and 100 ml of N,N-dimethylformamide-tetrahydrofuran (1:1) is cooled to 0° C., admixed with 0.800 g of sodium hydride dispersion (60%) and stirred over 30 minutes. The mixture is admixed with 7.90 g of (2-iodoethoxy)triisopropylsilane and stirred at room temperature for a further 16 hours. The reaction mixture is poured onto ice-water (150 ml) and extracted with ethyl acetate (3×150 ml). The organic phases are washed successively with aqueous sodium hydrogencarbonate solution (1×100 ml), water (100 ml) and brine (100 ml), dried over sodium sulphate, filtered and concentrated by evaporation. The title compound is obtained as a colourless oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.57 (1:1 EtOAc-heptane); Rt=6.71.

Workup

  1. stirringstirred at room temperature for a further 16 hours
  2. additionThe reaction mixture is poured onto ice-water (150 ml)
  3. extractionextracted with ethyl acetate (3×150 ml)
  4. washThe organic phases are washed successively with aqueous sodium hydrogencarbonate solution (1×100 ml), water (100 ml) and brine (100 ml)
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-29bd7d525a7d49cbbd7438f2bf1b91b5
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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