Water → FR 110302

HRID 1089237Notes

Reaction equation

HRID 1089237 reaction equation
[CH2:1]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[C:6]1=[O:27])[CH2:2][CH2:3][CH3:4].[BH4-].[Na+].O>CO>[CH2:1]([C:5]1([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:14][CH2:13][C:12]2[C:7](=[CH:8][CH:9]=[CH:10][C:11]=2[O:15][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[N:18]=2)[CH:6]1[OH:27])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydride3×HCID 105497902,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone

Product 1

HCID 164102FR 110302Yield 77.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,2-dibutyl-3,4-dihydro-5-(2-quinolylmethoxy)-1(2H)-naphthalenone (500 mg) in methanol (20 ml) was added sodium borohydride (68 mg) with stirring in an ice bath. The mixture was stirred for half an hour in an ice bath and then sodium borohydride (136 mg) was added thereto at the same temperature. The solution was stirred for 1.5 hours at ambient temperature, followed by the addition of sodium borohydride (68 mg). The mixture was stirred at ambient temperature for half an hour and then poured into water with stirring in an ice bath. The separated solid was collected by filtration, washed with water (50 ml), dried, and recrystallized from methanol to yield 2,2-dibutyl-5-(2-quinolylmethoxy)-1,2,3,4-tetrahydro-1-naphthol (388 mg).

Workup

  1. stirringThe mixture was stirred for half an hour in an ice bath
  2. stirringThe solution was stirred for 1.5 hours at ambient temperature
  3. stirringThe mixture was stirred at ambient temperature for half an hour
  4. stirringwith stirring in an ice bath
  5. filtrationThe separated solid was collected by filtration
  6. washwashed with water (50 ml)
  7. customdried
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-86c64c5e26ab41b3b1fce33e97dc6400
Source dataset
uspto-grants-1990_10
Patent number
US04965274

Reaction notes

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