Acetic Anhydride → 1-(3-Benzyloxy-6-methoxyphenyl)-1-(5-methoxy-2-pyridyl)-methyl acetate

HRID 346334Notes

Reaction equation

HRID 346334 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1.C([Li])CCC.[CH2:15]([O:22][C:23]1[CH:24]=[CH:25][C:26]([O:31][CH3:32])=[C:27]([CH:30]=1)[CH:28]=[O:29])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>N1C=CC=CC=1.CO>[C:33]([O:29][CH:28]([C:27]1[C:26]([O:31][CH3:32])=[CH:25][CH:24]=[C:23]([O:22][CH2:15][C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:30]=1)[C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][N:3]=1)(=[O:35])[CH3:34]

Participants

7

Reactant 4

HCID 7918Acetic AnhydrideHCID 109666945-(Benzyloxy)-2-methoxybenzaldehydeHCID 111481512-Bromo-5-methoxypyridineHCID 178418339Butyllithium

Product 1

HCID 143331241-(3-Benzyloxy-6-methoxyphenyl)-1-(5-methoxy-2-pyridyl)-methyl acetateYield 50%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 1049PyridineSolvent

Procedure

2-Bromo-5-methoxypyridine (15.35 g) was successively treated with n-butyl lithium and 5-benzyloxy -2-methoxybenzaldehyde (16.47 g, Example 1(i)) under the conditions of Example 1(j). The crude carbinol (19.4 g) was treated with acetic anhydride and pyridine as described in Example 1(k). The product was purified by column chromatography on silica gel (550 g). Elution with petroleum spirit (60-80°)/ethyl acetate (2:1), then recrystallisation from dichloromethane/petroleum spirit gave 1-(3-benzyloxy-6-methoxyphenyl)-1-(5-methoxy-2-pyridyl)-methyl acetate (13.29 g, 50%), m.p. 105-110°.

Workup

  1. customThe product was purified by column chromatography on silica gel (550 g)
  2. washElution with petroleum spirit (60-80°)/ethyl acetate (2:1)
  3. customrecrystallisation from dichloromethane/petroleum spirit

Sources & evidence

ORD record
ord-0f57a20cbc63486ca04d34d65ff9f1ef
Source dataset
uspto-grants-1991_10
Patent number
US05061798

Reaction notes

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