2-[(4-Nitrophenyl)methanesulfonyl]ethan-1-ol → HCID 15346011, compound

HRID 1864074Notes

Reaction equation

HRID 1864074 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([CH2:14][CH2:15][OH:16])(=[O:13])=[O:12])=[CH:6][CH:5]=1)([O-])=O>CO.[Pd]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([CH2:10][S:11]([CH2:14][CH2:15][OH:16])(=[O:13])=[O:12])=[CH:6][CH:5]=1

Participants

4

Reactant 1

HCID 135681992-[(4-Nitrophenyl)methanesulfonyl]ethan-1-ol2×

Product 1

HCID 15346011HCID 15346011, compoundYield 37%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A suspension of 2-{[(4-Nitrophenyl)methyl]sulfonyl}ethanol (Intermediate 148, 7.64 g, 46.3 mmol theoretical) and 10 wt % Pd/C (788 mg) in MeOH was stirred under an atmosphere of H2 at room temperature for 2 h, then filtered through a pad of celite. The filtrate was concentrated in vacuo, and the orange residue was recrystallized from MeOH/Et2O to give the desired product as light yellow crystals (3.65 g, 17.0 mmol, 37% over 3 steps). MS: M(C9H13NO3S)=215.27, (M+H)+=216.0.

Workup

  1. filtrationfiltered through a pad of celite
  2. concentrationThe filtrate was concentrated in vacuo
  3. customthe orange residue was recrystallized from MeOH/Et2O

Sources & evidence

ORD record
ord-9394706865dd44449fdebc5520ad54da
Source dataset
uspto-grants-2009_12
Patent number
US07625903B2

Reaction notes

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