Sodium borohydride → HCID 17966951, compound

HRID 1630775Notes

Reaction equation

HRID 1630775 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([S:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9])=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[CH:4]=[CH:5][C:6]([S:11][CH3:12])=[C:7]([CH:10]=1)[C:8]#[N:9]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 179666355-Formyl-2-(methylsulfanyl)benzonitrile

Product 1

HCID 17966951HCID 17966951, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

A flask is charged with 5-formyl-2-methylsulfanyl-benzonitrile (1.0 g, 5.68 mmol) in MeOH (20 mL) and cooled to 0° C. Sodium borohydride (1.07 g, 28.40 mmol) is added and the mixture is stirred at room temperature for 2 h, followed by removal of solvent in vacuo. The residue is re-dissolved in dichloromethane and washed with water twice. The organic layer is dried over sodium sulfate and concentrated in vacuo to afford 5-hydroxymethyl-2-methylsulfanyl-benzonitrile as a white solid. 1H NMR (400 MHz, CDCl3) δ ppm 2.57 (s, 3H), 4.70 (d, J=5.1 Hz, 2H), 7.33 (d, J=8.3 Hz, 1H), 7.53 (dd, J=8.3, 1.0 Hz, 1H), 7.62 (s, 1H).

Workup

  1. customfollowed by removal of solvent in vacuo
  2. dissolutionThe residue is re-dissolved in dichloromethane
  3. washwashed with water twice
  4. dry with materialThe organic layer is dried over sodium sulfate
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-cf5004dc586f4c6b98c7763d67ce1129
Source dataset
uspto-grants-2014_07
Patent number
US08791141B2

Reaction notes

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