Sodium borohydride → HCID 20523155, compound

HRID 223174Notes

Reaction equation

HRID 223174 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[O:7][CH:6]([CH2:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)[C:5]2=[O:17].[BH4-].[Na+]>CO>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[O:7][CH:6]([CH2:11][C:12]3[NH:16][CH:15]=[CH:14][N:13]=3)[CH:5]([OH:17])[C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 20523140HCID 20523140, compound

Product 1

HCID 20523155HCID 20523155, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Dissolve 5-chloro-2-(1'-imidazolylmethyl)coumaran-3-one (10 gms., 21 mmols.) in methanol (100 ml.), cool the solution to 0°-5° C. and add sodium borohydride (1.0 gms., 26.4 mmols.). Stir the reaction mixture overnight at room temperature and evaporate the methanol in vacuo. Add water (200 ml.) to the resultant residue and stir for 30 minutes. Filter and wash the resultant residue with water to give 5-chloro-2,3-dihydro-3-hydroxy-2-(1'-imidazolylmethyl)benzo(b)furan.

Workup

  1. temperaturecool the solution to 0°-5° C.
  2. customevaporate the methanol in vacuo
  3. stirringAdd water (200 ml.) to the resultant residue and stir for 30 minutes
  4. filtrationFilter
  5. washwash the resultant residue with water

Sources & evidence

ORD record
ord-d11e472a6d0e46d1be218b4085d24332
Source dataset
uspto-grants-1982_10
Patent number
US04352808

Reaction notes

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