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

HRID 863604노트

반응식

HRID 863604 반응식
[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]

참가 물질

5

반응물 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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e5e9d4ee00d8445eb5862852d81578fb
출처 데이터셋
uspto-grants-1998_02
특허 번호
US05721233

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