Sodium hydride → HCID 12967234, compound

HRID 1610041Notes

Reaction equation

HRID 1610041 reaction equation
[H-].[Na+].[CH3:3][C:4]([CH3:13])([CH:7]([OH:12])[C:8]([CH3:11])([CH3:10])[CH3:9])[CH2:5][OH:6].[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:6][CH2:5][C:4]([CH3:13])([CH3:3])[CH:7]([OH:12])[C:8]([CH3:11])([CH3:10])[CH3:9]

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 a nitrogen atmosphere, to a solution having 2.12 g (53.0 mmol) of 60% sodium hydride suspended in 80 ml of DMF at 0° C., 7.05 g (44.1 mmol) of 2,2,4,4-tetramethyl-1,3-pentanediol (compound (2)) dissolved in 15 ml of DMF, was dropwise added over a period of 30 minutes, followed by further stirring for 30 minutes. To this solution, 9.07 g (57.9 mmol) of 3-methoxybenzyl chloride (compound (1)) dissolved in 15 ml of DMF was dropwise added over a period of 30 minutes, followed by stirring for 12 hours. The reaction mixture was put into an aqueous saturated ammonium chloride solution and extracted with ethyl acetate. The extract layer was washed with a saturated sodium chloride aqueous solution, dried over anhydrous magnesium sulfate and then concentrated. The concentrated product was subjected to a silica gel column and eluted with a 10:1 mixed solvent of hexane and ethyl acetate, to obtain 10.7 g of 1-(3-methoxybenzyloxy)-2,2,4,4-tetramethyl-3-pentanol (compound (3)) in a yield of 86.7% as a colorless oily substance.

Workup

  1. additionwas dropwise added over a period of 30 minutes
  2. additionwas dropwise added over a period of 30 minutes
  3. stirringby stirring for 12 hours
  4. extractionextracted with ethyl acetate
  5. washThe extract layer was washed with a saturated sodium chloride aqueous solution
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. washeluted with a 10:1 mixed solvent of hexane and ethyl acetate

Sources & evidence

ORD record
ord-8cea5965883347b8a4227613defba1b1
Source dataset
uspto-grants-2006_01
Patent number
US06982336B2

Reaction notes

Loading…