Hydrochloric Acid → HCID 14404106, compound

HRID 465502Notes

Reaction equation

HRID 465502 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][N+:14]([O-:16])=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1)(O)=[O:2].Cl>O1CCCC1>[OH:2][CH2:1][C:4]1[CH:9]=[CH:8][C:7]([S:10]([CH2:13][N+:14]([O-:16])=[O:15])(=[O:12])=[O:11])=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 14404103HCID 14404103, compound

Product 1

HCID 14404106HCID 14404106, compoundYield 25.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Borane-methyl sulphide complex (0.1 ml, 1 mmol) was added to a solution of (4-carboxyphenylsulphonyl)nitromethane (0.25 g, 1 mmol) in anhydrous tetrahydrofuran (5 ml) and the mixture was stirred for 2 hours. The mixture was acidified with 2M hydrochloric acid to pH 1 and extracted with ethyl acetate. The combined extracts were dried (MgSO4) and the solvent was removed by evaporation. The residue was purified by MPLC eluting with methanol/dichloromethane (1:50 v/v) to give (4-hydroxymethylphenylsulphonyl)nitromethane (0.06 g) m.p. 73°-75° C.; microanalysis, found: C, 41.6; H, 3.9; N, 5.8%; C8H9NO5S requires: C, 41.6; H, 3.9; N, 6.1%.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined extracts were dried (MgSO4)
  3. customthe solvent was removed by evaporation
  4. customThe residue was purified by MPLC
  5. washeluting with methanol/dichloromethane (1:50 v/v)

Sources & evidence

ORD record
ord-75c3d65d7394459681bc7d10f53e5b14
Source dataset
uspto-grants-1992_10
Patent number
US05153227

Reaction notes

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