Trimethyl orthoformate → HCID 66990222, compound

HRID 454482Notes

Reaction equation

HRID 454482 reaction equation
[CH:1](OC)(OC)OC.[CH2:8]([O:15][C:16]1[CH:31]=[CH:30][C:29]([C:32]([NH:34][NH2:35])=[O:33])=[CH:28][C:17]=1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>>[CH2:8]([O:15][C:16]1[CH:31]=[CH:30][C:29]([C:32]2[O:33][CH:1]=[N:35][N:34]=2)=[CH:28][C:17]=1[C:18]([O:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[O:19])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=1

Participants

3

Reactant 2

HCID 9005Trimethyl orthoformateHCID 66990252HCID 66990252, compound

Product 1

HCID 66990222HCID 66990222, compound

Procedure

A trimethyl orthoformate (2 mL) suspension of the obtained benzyl 2-(benzyloxy)-5-(hydrazinocarbonyl)benzoate (0.20 g) was heated to reflux for 1 hour and 30 minutes. The reaction mixture was cooled to room temperature, and then the solvent was evaporated under reduced pressure. Ethyl acetate and diisopropyl ether were added to the obtained residue, and 0.16 g of the solid substance was collected by filtration. The obtained solid substance (0.11 g) was stirred at 200° C. for 15 minutes. The reaction mixture was cooled to room temperature and then purified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 90-50% hexane/ethyl acetate] to obtain 0.079 g of benzyl 2-(benzyloxy)-5-(1,3,4-oxadiazol-2-yl)benzoate as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 1 hour and 30 minutes
  3. customthe solvent was evaporated under reduced pressure
  4. additionEthyl acetate and diisopropyl ether were added to the obtained residue, and 0.16 g of the solid substance
  5. filtrationwas collected by filtration
  6. temperatureThe reaction mixture was cooled to room temperature
  7. custompurified by silica gel column chromatography [Kanto Chemical Co., Inc., silica gel 60 (spherical), eluent: 90-50% hexane/ethyl acetate]

Sources & evidence

ORD record
ord-23c557b058cb45e689f2fdff0700d6ab
Source dataset
uspto-grants-2013_07
Patent number
US08492582B2

Reaction notes

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