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

HRID 1165626Notes

Reaction equation

HRID 1165626 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-benzyloxy2-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). Eluion 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. customEluion with petroleum spirit (60-80° )/ethyl acetate (2:1), then recrystallisation from dichloromethane/petroleum spirit

Sources & evidence

ORD record
ord-10a0e0f4647545b8bc337fb334c5979a
Source dataset
uspto-grants-1990_03
Patent number
US04910305

Reaction notes

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