Triethylamine → HCID 22930436, compound

HRID 2247423Notes

Reaction equation

HRID 2247423 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[CH:10][C:9]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([O:20][CH3:21])=[O:19])[CH:13]=2)=[CH:8][C:4]=1[C:5](O)=[O:6].C(N(CC)CC)C.C(Cl)(=O)OCC>O1CCCC1>[OH:6][CH2:5][C:4]1[CH:8]=[C:9]([C:12]2[CH:13]=[C:14]([CH:15]=[CH:16][CH:17]=2)[C:18]([O:20][CH3:21])=[O:19])[CH:10]=[CH:11][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 59218967HCID 59218967, compound

Product 1

HCID 22930436HCID 22930436, compoundYield 58.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

894 mg of 2-Methoxy-5-[3-(methoxycarbonyl)phenyl]benzoic acid was dissolved in 7 ml of tetrahydrofuran, 0.36 mg of triethylamine and 0.55 ml of ethyl chlorocarbonate were added successively, and the mixture was stirred at room temperature for 15 minutes. The precipitated crystals were filtered, and the filtrate was filtered. 2 ml aqueous solution of 180 mg sodium borohydride was added thereto, and the mixture was stirred at room temperature for 1 hour. 1 N hydrochloric acid was added to the reaction mixture which was then extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed. The residue was purified by a silica gel column, to give 496 mg of the title compound in the 5:3 hexane-ethyl acetate fraction.

Workup

  1. filtrationThe precipitated crystals were filtered
  2. filtrationthe filtrate was filtered
  3. addition2 ml aqueous solution of 180 mg sodium borohydride was added
  4. stirringthe mixture was stirred at room temperature for 1 hour
  5. addition1 N hydrochloric acid was added to the reaction mixture which
  6. extractionwas then extracted with ethyl acetate
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. customthe solvent was removed
  9. customThe residue was purified by a silica gel column

Sources & evidence

ORD record
ord-2b2d27a1dc664cccae7745d4f75ea0b1
Source dataset
uspto-grants-2010_03
Patent number
US07687664B2

Reaction notes

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