Sodium borohydride → Benzenemethanol, 2-(2-naphthalenylthio)-

HRID 1066357Notes

Reaction equation

HRID 1066357 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH:14]=[O:15].[BH4-].[Na+]>CO.C1COCC1>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[S:11][C:12]1[CH:19]=[CH:18][CH:17]=[CH:16][C:13]=1[CH2:14][OH:15]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 21198703HCID 21198703, compound

Product 1

HCID 12228097Benzenemethanol, 2-(2-naphthalenylthio)-Yield 91.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To 2-(2-naphthylthio)benzaldehyde (7.24 g; 27.4 mmol from Example 6, step 1) in 70 mL of methanol and 30 mL of THF at 0° C. was added NaBH4 (54.8 mml) portionwise. After 1 h at 0° C., the solution was brought to r.t. and quenched with water. After dilution with EtOAc, the solution was washed with water and brine. The organic phase was dry over Na2SO4, filtered and the crude purified by silica gel chromatography to yield 6.71 g of the title compound.

Workup

  1. customwas brought to r.t.
  2. customquenched with water
  3. washAfter dilution with EtOAc, the solution was washed with water and brine
  4. dry with materialThe organic phase was dry over Na2SO4
  5. filtrationfiltered
  6. customthe crude purified by silica gel chromatography

Sources & evidence

ORD record
ord-10e74f4544c7492882b9545161b4f0b7
Source dataset
uspto-grants-2001_06
Patent number
US06242493B1

Reaction notes

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