Water → HCID 86745661, compound

HRID 1030250Notes

Reaction equation

HRID 1030250 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH3:20])[C:12](=[C:13]=[S:14])[C:11](=[C:15]=[S:16])[CH2:10][CH2:9][C:8]2=[CH:17][CH:18]=[O:19])[CH:2]=1.[BH4-].[Na+].C(OCC)(=O)C.O>CO>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2([CH3:20])[C:12](=[C:13]=[S:14])[C:11](=[C:15]=[S:16])[CH2:10][CH2:9][C:8]2=[CH:17][CH2:18][OH:19])[CH:2]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 57251425HCID 57251425, compound

Product 1

HCID 86745661HCID 86745661, compoundYield 66.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 2-(pyrid-3-yl)-2-methyldithiocarbonyl-1-formylmethylenecyclohexane (890 mg, 3 mmol) in methanol (20 ml) at 25° C. was treated with sodium borohydride (127 mg, 3.36 mmol). After 30 mins at 25° C. the solution was treated with ethyl acetate (50 ml) and water (20 ml) was added dropwise. The organic phase was removed and dried over magnesium sulphate. Concentration in vacuo yielded a crude oil. Purification over silica gel, eluting with ethyl acetate/n-hexane (7:3) afforded 2-(pyrid-3-yl)-2-methyldithiocarbonyl-1-(2-hydroxyethylidene)cyclohexane (590 mg, 2 mmol) as an orange solid, m.p. 139°-140° C.;

Workup

  1. additionwas added dropwise
  2. customThe organic phase was removed
  3. dry with materialdried over magnesium sulphate
  4. concentrationConcentration in vacuo
  5. customyielded a crude oil
  6. customPurification over silica gel
  7. washeluting with ethyl acetate/n-hexane (7:3)

Sources & evidence

ORD record
ord-4bc041e8f0ce4add9d7d1597d545707f
Source dataset
uspto-grants-1992_04
Patent number
US05104883

Reaction notes

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