Sodium borohydride → HCID 22413568, compound

HRID 1721677Notes

Reaction equation

HRID 1721677 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[C:19](=[O:23])[CH2:18][CH2:17][CH2:16]2.[BH4-].[Na+]>C(O)C>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH2:11][O:12][C:13]1[CH:14]=[C:15]2[C:20](=[CH:21][CH:22]=1)[CH:19]([OH:23])[CH2:18][CH2:17][CH2:16]2

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 22413579HCID 22413579, compound

Product 1

HCID 22413568HCID 22413568, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 3,4-dihydro-6-(2-quinolylmethoxy)-1(2H)-naphthalenone (1.82 g, 6 mmol), prepared as in step 2, and sodium borohydride (230 mg, 6 mmol) in ethanol (15 mL) was refluxed for 30 minutes. The reaction was allowed to warm to ambient temperature and was then quenched with saturated NH4Cl. Extraction with ethyl acetate and purification on a silica gel column eluting with 9:1 CH2Cl2 -ethyl acetate afforded 1.79 g of 1,2,3,4-tetrahydro-6-(2-quinolylmethoxy)-1-naphthalenol.

Workup

  1. temperaturewas refluxed for 30 minutes
  2. customwas then quenched with saturated NH4Cl
  3. extractionExtraction
  4. customwith ethyl acetate and purification on a silica gel column
  5. washeluting with 9:1 CH2Cl2 -ethyl acetate

Sources & evidence

ORD record
ord-46e7568f9f5948ca864b76f6017de91d
Source dataset
uspto-grants-1996_04
Patent number
US05512581

Reaction notes

Loading…