Methanol → {4-[2-(Dimethylamino)ethoxy]phenyl}methanol

HRID 612815Notes

Reaction equation

HRID 612815 reaction equation
[BH4-].[Na+].[CH3:3][CH2:4][O:5][C:6]([CH3:8])=O.CC[CH2:11][CH2:12][CH2:13][CH3:14].[CH2:15]([N:17]([CH2:20]C)CC)C.[CH3:22][OH:23]>O>[CH3:15][N:17]([CH3:20])[CH2:3][CH2:4][O:5][C:6]1[CH:8]=[CH:14][C:13]([CH2:22][OH:23])=[CH:12][CH:11]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 22141343EtOAc hexane triethylamine

Product 1

HCID 10176517{4-[2-(Dimethylamino)ethoxy]phenyl}methanolYield 88%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a stirred solution of the aldehyde 2c (5.9 g, 0.031 mol, 1.0 eq.) in methanol (20 mL) at 22° C. sodium borohydride (0.58 g, 0.015 mol, 0.5 eq.) is added in portions. The reaction is stirred for 30 min. TLC at this point shows no starting material, mostly product (EtOAc/hexane/triethylamine 5:5: 1). The reaction mixture is diluted with water (50 mL), extracted with methylene chloride (3×40 mL), and dried over MgSO4. The solution is concentrated on a rotary evaporator to give 5.25 g (88%) of the alcohol 3c as a thick oil.

Workup

  1. extractionextracted with methylene chloride (3×40 mL)
  2. dry with materialdried over MgSO4
  3. concentrationThe solution is concentrated on a rotary evaporator

Sources & evidence

ORD record
ord-ba03422de9624a24b83b453cc5c70760
Source dataset
uspto-grants-1999_12
Patent number
US06005102

Reaction notes

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