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

HRID 346334노트

반응식

HRID 346334 반응식
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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 887Methanol용매HCID 1049Pyridine용매

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-0f57a20cbc63486ca04d34d65ff9f1ef
출처 데이터셋
uspto-grants-1991_10
특허 번호
US05061798

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