Sodium hydride → 1,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione

HRID 53898ノート

反応式

HRID 53898 の反応式
[NH:1]1[C:5]2[C:6](=[O:12])[NH:7][CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1.[H-].[Na+].[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22]Cl)([CH3:18])[CH3:17].[Cl-].[NH4+]>CN(C)C=O>[CH3:15][Si:16]([CH2:19][CH2:20][O:21][CH2:22][N:1]1[C:5]2[C:6](=[O:12])[N:7]([CH2:22][O:21][CH2:20][CH2:19][Si:16]([CH3:18])([CH3:17])[CH3:15])[CH2:8][CH2:9][C:10](=[O:11])[C:4]=2[CH:3]=[CH:2]1)([CH3:18])[CH3:17]

参加物

6

反応物 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 3085877Aldisine

生成物 1

HCID 110589801,7-di(trimethylsilylethoxymethyl)-6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione収率 48%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

A 500 mg amount of the 6,7-dihydropyrrolo[2,3-c]azepin-4,8(1H, 5H)dione (aldisin) described in the reference (Prager, R. et al: Aust. J. Chem., 43, p. 355-365 (1990)) was added to a 20 ml dimethylformamide suspension of 252 mg of sodium hydride (60% oil). The mixture was stirred at room temperature for 1 hour. A 1.12 ml amount of trimethylsilylethoxymethyl chloride was added under ice cooling, the mixture was stirred at room temperature for 3 hours, then a saturated aqueous solution of ammonium chloride was added and extraction was performed by ethyl acetate. The extract was washed with saturated saline, dried, filtered, and concentrated under reduced pressure to obtain a residue which was purified by silica gel column chromatography (hexane:ether acetate=6:1) to obtain 623 mg of the above-referenced compound (8) (yield 48%).

後処理

  1. stirringthe mixture was stirred at room temperature for 3 hours
  2. extractionextraction
  3. washThe extract was washed with saturated saline
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customto obtain a residue which
  8. customwas purified by silica gel column chromatography (hexane:ether acetate=6:1)

出典と根拠

ORDレコード
ord-1c18622ef01b47798c68d59f65e97b4b
出典データセット
uspto-grants-1997_04
特許番号
US05621099

反応ノート

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