Sodium borohydride → 3-(N,N-Dimethylsulfamoyl)-4-methoxybenzyl alcohol

HRID 901193

Reaction equation

HRID 901193 reaction equation
[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH:9]=[O:10])(=[O:5])=[O:4].[BH4-].[Na+]>C1COCC1>[CH3:1][N:2]([CH3:16])[S:3]([C:6]1[CH:7]=[C:8]([CH:11]=[CH:12][C:13]=1[O:14][CH3:15])[CH2:9][OH:10])(=[O:4])=[O:5]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 219769013-(N,N-Dimethylsulfamoyl)-4-methoxybenzaldehyde

Product 1

HCID 657511993-(N,N-Dimethylsulfamoyl)-4-methoxybenzyl alcoholYield 62.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of OBS02049 (5.5 g, 21.21 mmol) in anhydrous THF (50 mL) was added sodium borohydride (0.88 g, 23.33 mmol). The mixture was stirred at room temperature for 4 h, quenched with water (CARE!!) and filtered through a Celite pad. The filtrate was concentrated in vacuo and re-dissolved in DCM (200 mL). The organic layer was washed with brine (2×200 mL), dried (Na2SO4) and filtered. Concentration in vacuo of the combined filtrates gave OBS02053 as a golden-yellow oil (3.26 g, 59%). TLC [SiO2, EtOAc-n-hexane (1:1)] Rf=0.36; 1H-NMR (270 MHz, CDCl3)=1.73 (1H, bs, OH), 2.97 (6H, s), 3.88 (3H, s), 4.62 (2H, s), 6.95 (1H, d, J=8.4), 7.23 (1H, dd, J=2.2, 8.4), 7.36 (1H, d, J=2.2).

Workup

  1. customquenched with water (CARE!!)
  2. filtrationfiltered through a Celite pad
  3. concentrationThe filtrate was concentrated in vacuo
  4. dissolutionre-dissolved in DCM (200 mL)
  5. washThe organic layer was washed with brine (2×200 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationConcentration in vacuo of the combined filtrates

Sources & evidence

ORD record
ord-bdeaae6020d248a990c566482be9954a
Source dataset
uspto-grants-2008_04
Patent number
US07361677B2

Linked notes

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