Acetic Anhydride → HCID 86660320, compound

HRID 1849950Notes

Reaction equation

HRID 1849950 reaction equation
C(N(CC)CC)C.[CH2:8]1[CH2:12][O:11]CC1.[OH:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22](=[O:46])[CH:23]([CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])[C:24](=[O:39])[CH:25]=[CH:26][C:27]2[CH:32]=[CH:31][C:30]([OH:33])=[C:29]([O:34][C:35]([F:38])([F:37])[F:36])[CH:28]=2)=[CH:16][C:15]=1[O:47][C:48]([F:51])([F:50])[F:49].[C:52](OC(=O)C)(=[O:54])[CH3:53]>O>[C:52]([O:33][C:30]1[CH:31]=[CH:32][C:27]([CH:26]=[CH:25][C:24](=[O:39])[CH:23]([CH2:40][CH2:41][C:42]([O:44][CH3:45])=[O:43])[C:22](=[O:46])[CH:21]=[CH:20][C:17]2[CH:18]=[CH:19][C:14]([O:13][C:12](=[O:11])[CH3:8])=[C:15]([O:47][C:48]([F:49])([F:50])[F:51])[CH:16]=2)=[CH:28][C:29]=1[O:34][C:35]([F:37])([F:38])[F:36])(=[O:54])[CH3:53]

Participants

6

Reactant 4

HCID 7918Acetic AnhydrideHCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 86660321HCID 86660321, compound

Product 1

HCID 86660320HCID 86660320, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

Triethylamine 270 mg was added under room temperature to a THF 10 mL solution containing 1,7-bis(4′-hydroxy-3′-trifluoromethoxyphenyl)-4-methoxycarbonylethyl 1,6-heptadiene 3,5-dione 500 mg and acetic anhydride 272 mg, and the resultant solution was agitated for 2 hours at room temperature. After the reaction was ended, water was poured, and the resultant solution was subjected to extraction with ethyl acetate. The extract was dried with sodium sulfate, and the solvent was removed. The crystal residue was washed with a small quantity of ethanol, filtered, and dried, whereby 430 mg of 1,7-bis(4′-acetoxy-3′-trifluoromethoxyphenyl)-4-methoxycarbonylethyl-1,6-heptadiene-3,5-dione having a melting point of 149 to 150° C. was obtained.

Workup

  1. extractionthe resultant solution was subjected to extraction with ethyl acetate
  2. dry with materialThe extract was dried with sodium sulfate
  3. customthe solvent was removed
  4. washThe crystal residue was washed with a small quantity of ethanol
  5. filtrationfiltered
  6. customdried

Sources & evidence

ORD record
ord-20cfd927a22645a4b73c7073dc782833
Source dataset
uspto-grants-2015_02
Patent number
US08956589B2

Reaction notes

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