Sodium hydride → HCID 86703881, compound

HRID 471440Notes

Reaction equation

HRID 471440 reaction equation
[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([OH:9])=[CH:4][C:3]=1[CH3:10].[H-].[Na+].[CH3:13][S:14]([C:17]([CH3:25])([CH3:24])[CH2:18]OS(C)(=O)=O)(=[O:16])=[O:15]>CN(C)C=O>[Br:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([O:9][CH2:18][C:17]([S:14]([CH3:13])(=[O:16])=[O:15])([CH3:25])[CH3:24])=[CH:4][C:3]=1[CH3:10]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 819704-Bromo-3,5-dimethylphenolHCID 867038821-Propanol, 2-methyl-2-(methylsulfonyl)-, 1-methanesulfonate

Product 1

HCID 86703881HCID 86703881, compoundYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
160 °C

Procedure

4-Bromo-3,5-dimethylphenol (1.3 g, 6.51 mmol) and NaH (60% on mineral oil: 167 mg, 4.17 mmol) are stirred in 8 mL of N,N-dimethylformamide for 30 min in a microwave vial, methanesulfonic acid 2-methanesulfonyl-2-methyl-propyl ester (600 mg, 2.61 mmol) is added and the reaction mixture is heated in a microwave oven at 160° C. for 2 h. The solvent is removed under vacuum and the crude product is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→90/10) to give the title compound (Yield: 250 mg).

Workup

  1. additionis added
  2. customThe solvent is removed under vacuum
  3. customthe crude product is purified by flash chromatography (cyclohexane/ethyl acetate 99/01→90/10)

Sources & evidence

ORD record
ord-a47e308c214342638a444d3476826d49
Source dataset
uspto-grants-2014_01
Patent number
US08633182B2

Reaction notes

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