Sodium hydride → HCID 69245544, compound

HRID 2371102Notes

Reaction equation

HRID 2371102 reaction equation
[C:1]([O:5][C:6](=[O:19])[CH2:7][C:8](=[O:18])[CH2:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([Br:17])=[CH:13][CH:12]=1)([CH3:4])([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:23][CH2:24][O:25][Si:26]([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]>CN(C)C=O>[CH3:30][C:29]([Si:26]([CH3:28])([CH3:27])[O:25][CH2:24][CH2:23][CH:7]([C:8](=[O:18])[CH2:9][CH2:10][C:11]1[CH:12]=[CH:13][C:14]([Br:17])=[CH:15][CH:16]=1)[C:6]([O:5][C:1]([CH3:4])([CH3:2])[CH3:3])=[O:19])([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3608067(2-Bromoethoxy)-tert-butyldimethylsilaneHCID 66671407HCID 66671407, compound

Product 1

HCID 69245544HCID 69245544, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
70 °C

Procedure

A solution of the compound (9.7 g) obtained from step 1 above in dimethylformamide (25 ml) was added dropwise over 20 minutes to a stirred suspension of sodium hydride (1.42 g) in dimethylformamide (25 ml) at 0° C. under nitrogen atmosphere and stirred the reaction mixture for 20 minutes. To it was added (2-bromoethoxy)-t-butyldimethylsilane (8.50 g) dropwise over 20 minutes at 0° C. then the reaction mixture was heated to 70° C. for about 3-4 hour. On cooling to room temperature the reaction was quenched with water. The residue was partitioned between saturated aqueous ammonium chloride solution and dichloromethane. The organic phases were combined, washed with water and brine, dried over anhydrous sodium sulphate and concentrated under reduced pressure. The residue thus obtained was purified by column chromatography using 8% ethyl acetate in hexane as eluant to furnish the title compound (9.5 g).

Workup

  1. temperatureOn cooling to room temperature the reaction
  2. customwas quenched with water
  3. customThe residue was partitioned between saturated aqueous ammonium chloride solution and dichloromethane
  4. washwashed with water and brine
  5. dry with materialdried over anhydrous sodium sulphate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue thus obtained
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-7f67bfbc7ec24838911558e9851143a4
Source dataset
uspto-grants-2014_04
Patent number
US08710261B2

Reaction notes

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