Sodium hydride → HCID 12967234, compound

HRID 324173Notes

Reaction equation

HRID 324173 reaction equation
[CH3:1][C:2]([CH3:11])([CH:5]([OH:10])[C:6]([CH3:9])([CH3:8])[CH3:7])[CH2:3][OH:4].[H-].[Na+].[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19]Cl.[Cl-].[NH4+]>CN(C=O)C>[CH3:14][O:15][C:16]1[CH:17]=[C:18]([CH:21]=[CH:22][CH:23]=1)[CH2:19][O:4][CH2:3][C:2]([CH3:11])([CH3:1])[CH:5]([OH:10])[C:6]([CH3:9])([CH3:8])[CH3:7]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 699943-Methoxybenzyl chloride2×HCID 15858524HCID 15858524, compound2×

Product 1

HCID 12967234HCID 12967234, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent3×

Procedure

In nitrogen atmosphere, adding dropwise 15 ml of DMF dissolving 7.05 g (44.1 mmol) of 2,2,4,4-tetramethyl-1,3-pentandiol (Compound [2]) to 80 ml of DMF suspended with 2.12 g (53.0 mmol) of 60% sodium hydride over 30 minutes, then the mixture was stirred for 30 minutes. After adding dropwise 15 ml of DMF dissolving 9.07 g (57.9 mmol) of 3-methoxybenzylchoride (Compound [47]) to the mixture over 30 minutes, the mixture was stirred for 12 hours. The reaction mixture was added to saturated aqueous solution of ammonium chloride and extracted with ethyl acetate. The organic layer was washed with saturated aqueous solution of sodium chloride, then dried with magnesium sulfate anhydride and concentrated. The concentrate was applied to a silica gel column and the elution was carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1) to obtain 10.7 g of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanol (Compound [48]) as a colorless oil. Yield 86.7%.

Workup

  1. stirringthe mixture was stirred for 12 hours
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with saturated aqueous solution of sodium chloride
  4. dry with materialdried with magnesium sulfate anhydride
  5. concentrationconcentrated
  6. washthe elution
  7. additionwas carried out with the mixture of hexane and ethyl acetate (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-a23ad8832a8e4692811c5c0175affb44
Source dataset
uspto-grants-2001_04
Patent number
US06218135B1

Reaction notes

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