Sodium borohydride → HCID 53944516, compound

HRID 726177Notes

Reaction equation

HRID 726177 reaction equation
[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][C:10]2=[O:15])=[O:4].[BH4-].[Na+]>C(O)C>[CH3:1][O:2][C:3]([C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:14]=1[S:13][CH2:12][CH2:11][CH:10]2[OH:15])=[O:4]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 130039219HCID 130039219, compound

Product 1

HCID 53944516HCID 53944516, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Methylthiochroman-4-one-8-carboxylate (0.500 g, 2.25mmol) was dissolved with stirring in ethanol (20 ml) and treated with sodium borohydride (0.085 g, 2.25 mmol). After 1 h, the reaction mixture was evaporated under reduced pressure and the residue partitioned between ethyl acetate and water. The aqueous layer was then extracted with ethyl acetate (1 x) and the combined organic layers were dried (Na2SO4) and evaporated under reduced pressure to give a yellow oil, which was purified by silica-gel chromatography (1:1 Pentane:EtOAc as eluant) to give the title compound as a colourless oil (0.499 g, 99%)

Workup

  1. customthe reaction mixture was evaporated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. extractionThe aqueous layer was then extracted with ethyl acetate (1 x)
  4. dry with materialthe combined organic layers were dried (Na2SO4)
  5. customevaporated under reduced pressure
  6. customto give a yellow oil, which
  7. customwas purified by silica-gel chromatography (1:1 Pentane:EtOAc as eluant)

Sources & evidence

ORD record
ord-5640b55abd2342b98d780d8ad7459911
Source dataset
uspto-grants-1998_01
Patent number
US05708174

Reaction notes

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