Sodium borohydride → HCID 10767637, compound

HRID 1378395Notes

Reaction equation

HRID 1378395 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:18]=[CH:17][C:16]([C:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:23][CH:22]=2)=[O:20])=[CH:15][CH:14]=1.[BH4-].[Na+]>C1COCC1.CO>[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:18]=[CH:17][C:16]([CH:19]([C:21]2[CH:26]=[CH:25][C:24]([O:27][CH2:28][C:29]3[CH:38]=[CH:37][C:36]4[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=4)[N:30]=3)=[CH:23][CH:22]=2)[OH:20])=[CH:15][CH:14]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 10505429HCID 10505429, compound

Product 1

HCID 10767637HCID 10767637, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

To a solution of bis(4(2-quinolylmethoxy)phenyl ketone (1.25 g, 2.5 mmol), prepared as in step 1, in THF/CH3OH (1:1, 60 mL) at room temperature was added NaBH4 (0.37 g, 10 mmol) and the mixture was refluxed for 3 hours, concentrated in vacuo, suspended in water and neutralized with citric acid. The resulting precipitate was collected by filtration, washed with 20% Et2O/hexane and dried in vacuo to afford bis(4-(2-quinolylmethoxy)phenyl)methanol (1.1 g, 88%) as white solid.

Workup

  1. temperaturethe mixture was refluxed for 3 hours
  2. concentrationconcentrated in vacuo
  3. filtrationThe resulting precipitate was collected by filtration
  4. washwashed with 20% Et2O/hexane
  5. customdried in vacuo

Sources & evidence

ORD record
ord-fd7f251bf494409eb3a5d879ac6bcd38
Source dataset
uspto-grants-1997_09
Patent number
US05668146

Reaction notes

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