Sodium borohydride → HCID 86584894, compound

HRID 1058991Notes

Reaction equation

HRID 1058991 reaction equation
ClC1C=CC([C:8]2[C:9](=[O:26])[CH:10]=[C:11]([CH:24]=[O:25])[O:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=CC=1.[BH4-].[Na+]>CO>[OH:25][CH2:24][C:11]1[O:12][C:13]([C:14]2[CH:19]=[CH:18][C:17]([S:20]([CH3:23])(=[O:22])=[O:21])=[CH:16][CH:15]=2)=[CH:8][C:9](=[O:26])[CH:10]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 18669509HCID 18669509, compound

Product 1

HCID 86584894HCID 86584894, compoundYield 69.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-(4-chlorophenyl)-6-(4-methanesulfonylphenyl)-4-oxo-4H-pyran-2-carbaldehyde (1.8 g, 4.6 mmoles) in methanol (30 ml), sodium borohydride (0.26 g, 6.9 mmoles)was slowly added at 0° C. The resulting mixture was stirred for 30 minutes at room temperature. The reaction mixture was concentrated and the residue was solved in ethyl acetate. The organic layer was washed with water, dried (Na2SO4), and the solvent was removed under reduced pressure. The resulting residue was purified by column chromatography with silica gel and ethyl acetate/n-hexane (1:1) as eluent. 3-4-chlorophenyl)-6-hydroxymethyl-2-(4-methanesulfonylphenyl)pyran-4-one (0.9 g) was obtained. m.p. 120° C. (Compound 60 in Table 4).

Workup

  1. concentrationThe reaction mixture was concentrated
  2. washThe organic layer was washed with water
  3. dry with materialdried (Na2SO4)
  4. customthe solvent was removed under reduced pressure
  5. customThe resulting residue was purified by column chromatography with silica gel and ethyl acetate/n-hexane (1:1) as eluent

Sources & evidence

ORD record
ord-861316afd28c413baaeab8d5721a4ea5
Source dataset
uspto-grants-2003_02
Patent number
US06518303B2

Reaction notes

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