Sodium borohydride → HCID 15718590, compound

HRID 654229Notes

Reaction equation

HRID 654229 reaction equation
[C:1]([CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[C:4]1=[O:15])#[N:2].[BH4-].[Na+]>CO>[C:1]([CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[O:13][CH3:14])[CH:4]1[OH:15])#[N:2]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 12231028HCID 12231028, compound

Product 1

HCID 15718590HCID 15718590, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The compound obtained in step (iii) above (16.2 g, 0.080 mol) is reduced with sodium borohydride (3.1 g, 0.082 mol) in absolute methanol (500 ml). The reaction mixture is concentrated under vacuum, ice-water is added thereto, the mixture is made acidic by the addition of concentrated hydrochloric acid and extracted with ethyl acetate. Upon evaporation of the solvent 2-cyano-5-methoxy-1,2,3,4-tetrahydro-1-naphthol (16.2 g) is obtained; m.p. 96°-98° C.

Workup

  1. concentrationThe reaction mixture is concentrated under vacuum, ice-water
  2. additionis added
  3. additionthe mixture is made acidic by the addition of concentrated hydrochloric acid
  4. extractionextracted with ethyl acetate
  5. customUpon evaporation of the solvent 2-cyano-5-methoxy-1,2,3,4-tetrahydro-1-naphthol (16.2 g)
  6. customis obtained

Sources & evidence

ORD record
ord-75ef0e66fb554c3d8fa520277dc76cb0
Source dataset
uspto-grants-1992_07
Patent number
US05130339

Reaction notes

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