Sodium borohydride → [3-(2-Methanesulphinyl-ethoxy)-phenyl]-methanol

HRID 1046359Notes

Reaction equation

HRID 1046359 reaction equation
[CH3:1][S:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH:12]=[CH:13][CH:14]=1)[CH:10]=[O:11])=[O:3].[BH4-].[Na+]>C(O)C>[CH3:1][S:2]([CH2:4][CH2:5][O:6][C:7]1[CH:8]=[C:9]([CH2:10][OH:11])[CH:12]=[CH:13][CH:14]=1)=[O:3]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 592591793-(2-Methanesulphinyl-ethoxy)-benzaldehyde

Product 1

HCID 59259025[3-(2-Methanesulphinyl-ethoxy)-phenyl]-methanol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1.1 g (5.18 mmol) 3-(2-methanesulphinyl-ethoxy)-benzaldehyde in 20 ml ethanol (anhydrous) is added NaBH4 (0.215 g, 5.7 mmol). The reaction mixture is stirred at room temperature for 0.5 h. Then it is poured onto water and extracted with ethyl acetate. The combined organic layers are washed with water and brine, dried over MgSO4, filtered and concentrated in vacuo to afford the title compound as a colorless oil that is of sufficient purity for the next step.

Workup

  1. additionThen it is poured onto water
  2. extractionextracted with ethyl acetate
  3. washThe combined organic layers are washed with water and brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5650063affcf4468b9a1d868358aa9ac
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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