Trimethyl orthoformate → 2,3-Dihydro-5-(4-nitrobenzoyl)oxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid, methyl ester

HRID 863604ノート

反応式

HRID 863604 の反応式
[N+:1]([C:4]1[CH:28]=[CH:27][C:7]([C:8]([O:10][C:11]2[C:12]([CH3:26])=[C:13](C)[C:14]3[O:19][C:18]([CH3:21])([CH3:20])[CH2:17][C:16](=O)[C:15]=3[C:23]=2[CH3:24])=[O:9])=[CH:6][CH:5]=1)([O-:3])=[O:2].O.O.O.[N+]([O-])([O-])=O.[Tl+3].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.CO[CH:47]([O:50]C)[O:48][CH3:49]>CO>[N+:1]([C:4]1[CH:5]=[CH:6][C:7]([C:8]([O:10][C:11]2[C:23]([CH3:24])=[C:15]([CH3:16])[C:14]3[O:19][C:18]([CH3:20])([CH3:17])[CH:21]([C:47]([O:48][CH3:49])=[O:50])[C:13]=3[C:12]=2[CH3:26])=[O:9])=[CH:27][CH:28]=1)([O-:3])=[O:2]

参加物

5

反応物 3

HCID 9005Trimethyl orthoformateHCID 11270721Nitric acid,thallium(3+) salt, trihydrate (9CI)HCID 152275713,4-dihydro-6-(4-nitrobenzoyl)oxy-2,2,5,7,8-pentamethyl-2H-1-benzopyran-4-one

生成物 1

HCID 103416402,3-Dihydro-5-(4-nitrobenzoyl)oxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid, methyl ester収率 84%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A heterogeneous mixture of 30.20 g (0.079 mol) of 3,4-dihydro-6-(4-nitrobenzoyl)oxy-2,2,5,7,8-pentamethyl-2H-1-benzopyran-4-one, 36.86 g (0.083 m) of thallium (III) nitrate trihydrate, 200 ml of trimethylorthoformate, and 200 ml of methanol is stirred at room temperature for 4 days. The resulting solid is collected and washed with methanol. The residue is slurried in 100 ml of chloroform and filtered; this process is repeated three times. The combined filtrates are heated to boiling and the chloroform is gradually replaced by an equal volume of methanol until crystallization occurs to give 27.44 g (84%) of 2,3-dihydro-5-(4-nitrobenzoyl)oxy-2,2,4,6,7-pentamethyl-1-benzofuran-3-carboxylic acid, methyl ester, m.p. 215°-216° C. Elemental analysis, IR, UV, and 1H-NMR spectra confirm the structure. This procedure was scaled up to 402 g, and 380.9 g (87.8%) of product was obtained.

後処理

  1. customThe resulting solid is collected
  2. washwashed with methanol
  3. filtrationfiltered
  4. temperatureThe combined filtrates are heated
  5. customthe chloroform is gradually replaced by an equal volume of methanol until crystallization

出典と根拠

ORDレコード
ord-e5e9d4ee00d8445eb5862852d81578fb
出典データセット
uspto-grants-1998_02
特許番号
US05721233

反応ノート

読み込み中…