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

HRID 346334ノート

反応式

HRID 346334 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 887Methanol溶媒HCID 1049Pyridine溶媒

実験手順

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°.

後処理

  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

出典と根拠

ORDレコード
ord-0f57a20cbc63486ca04d34d65ff9f1ef
出典データセット
uspto-grants-1991_10
特許番号
US05061798

反応ノート

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