Ethoxyquin → 1-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline

HRID 1995055

反応式

HRID 1995055 の反応式
[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[C:8]2[C:10]([CH3:16])=[CH:11][C:12]([CH3:15])([CH3:14])[NH:13][C:7]2=[CH:6][CH:5]=1.[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[C@@H:24]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:23][C@@H:22]1Br)(=[O:19])[CH3:18]>CC(C)=O>[C:17]([O:20][C@@H:21]1[C@@H:26]([O:27][C:28](=[O:30])[CH3:29])[C@H:25]([O:31][C:32](=[O:34])[CH3:33])[C@@H:24]([CH2:35][O:36][C:37](=[O:39])[CH3:38])[O:23][CH:22]1[N:13]1[C:7]2[C:8](=[CH:9][C:4]([O:3][CH2:2][CH3:1])=[CH:5][CH:6]=2)[C:10]([CH3:16])=[CH:11][C:12]1([CH3:15])[CH3:14])(=[O:19])[CH3:18]

参加物

4

反応物 2

HCID 3293EthoxyquinHCID 101776alpha-D-Glucopyranosyl bromide, tetraacetate

生成物 1

HCID 131953191-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline収率 74.6%

試薬・触媒・溶媒 1

HCID 180Acetone溶媒

実験手順

Ethoxyquin (240 g) and 2,3,4,6-tetra-O-acetyl-α-D-glucopyranosyl bromide (228 g) were stirred at 80° for 18 hours. Acetone (200 ml) was added to the hot reaction mixture and stirring continued for an additional 20 minutes. After cooling, the solid ethoxyquin hydrobromide was filtered off, washed thoroughly with acetone and the combined acetone filtrates were evaporated under reduced pressure. The resulted crude product was recrystallised (iso-propanol) to yield 226.5 g of 1-(2,3,4,6-tetra-O-acetyl-D-glucopyranosyl)-6-ethoxy-1,2-dihydro-2,2,4-trimethylquinoline. m.p.: 180°-181°.

後処理

  1. temperatureAfter cooling
  2. filtrationthe solid ethoxyquin hydrobromide was filtered off
  3. washwashed thoroughly with acetone
  4. customthe combined acetone filtrates were evaporated under reduced pressure
  5. customThe resulted crude product
  6. customwas recrystallised (iso-propanol)

出典と根拠

ORDレコード
ord-2dd5c332b340495ba622b6c4fb8309e5
出典データセット
uspto-grants-1983_09
特許番号
US04402945

関連ノート

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