Sodium Hydroxide → (+/-)-alpha-(6-(Benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanol

HRID 1600906Notes

Reaction equation

HRID 1600906 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]2)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:21][CH:22]([OH:31])[CH2:23][CH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1.[OH-].[Na+]>C(O)C.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([O:19][CH2:21][CH:22]([OH:31])[CH2:23][CH2:24][C:25]1[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=1)[CH:13]=[CH:12]2)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 144964736-(Benzyloxy)naphthalen-2-OLHCID 22465338HCID 22465338, compound

Product 1

HCID 21830659(+/-)-alpha-(6-(Benzyloxy)-2-naphthyloxymethyl)-3-pyridinepropanolYield 25.6%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

Prepared according to the method described in Example 24b) from 6-(benzyloxy)-2-naphthol (2.2 g; Chem. Ber., (1965) 98, 1233), (±)-α-(chloromethyl)-3-pyridinepropanol (1.89 g; from Example 24a) above) and sodium hydroxide (0.8 g) in ethanol (30 ml) and water (10 ml) with heating at reflux for 6 hours to give the title compound as a solid (0.9 g).

Workup

  1. customPrepared
  2. temperaturewith heating
  3. temperatureat reflux for 6 hours

Sources & evidence

ORD record
ord-eb4bc1c686b441ee848f04639229b635
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

Loading…