Sodium borohydride → HCID 178486576, compound

HRID 428618Notes

Reaction equation

HRID 428618 reaction equation
[NH:1]1[CH:5]=[C:4]([CH:6]2[C:14]3[C:9](=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([O:15][CH3:16])[CH:13]=3)[C:8](=[O:19])[CH2:7]2)[N:3]=[CH:2]1.[BH4-].[Na+]>C(O)C>[NH:1]1[CH:5]=[C:4]([CH:6]2[C:14]3[C:9](=[C:10]([CH3:18])[C:11]([CH3:17])=[C:12]([O:15][CH3:16])[CH:13]=3)[CH:8]([OH:19])[CH2:7]2)[N:3]=[CH:2]1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 178486575HCID 178486575, compound

Product 1

HCID 178486576HCID 178486576, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
37.5 °C

Procedure

3-(1H-Imidazol-4-yl)-5-methoxy-6,7-dimethylindan-1-one (0.53 g) is dissolved in ethanol (30 ml) and 0.3 g of sodium borohydride is added. The mixture is stirred at 35-40° C. for 7 hours. About 20 ml of ethanol is then distilled off and 30 ml of water is added. The solution is extracted with ethyl acetate. The combined ethyl acetate extracts are washed with water, dried with sodium sulfate, and evaporated under reduced pressure. The product is the mixture of cis- and trans-isomers (about 85:15). Crystallization of the product from ethyl acetate gives a cis-isomer, m.p. 184-189° C.

Workup

  1. distillationAbout 20 ml of ethanol is then distilled off
  2. addition30 ml of water is added
  3. extractionThe solution is extracted with ethyl acetate
  4. washThe combined ethyl acetate extracts are washed with water
  5. dry with materialdried with sodium sulfate
  6. customevaporated under reduced pressure
  7. additionthe mixture of cis- and trans-isomers (about 85:15)
  8. customCrystallization of the product from ethyl acetate
  9. customgives a cis-isomer, m.p. 184-189° C.

Sources & evidence

ORD record
ord-a6ce9148eb954969ba7084d9689eddde
Source dataset
uspto-grants-2001_11
Patent number
US06313311B1

Reaction notes

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