Hydrochloric Acid → HCID 57661209, compound

HRID 384599Notes

Reaction equation

HRID 384599 reaction equation
[CH3:1][O:2][C:3]1[CH:19]=[CH:18][C:6]([C:7]([C:9]23[O:16][C:15](=[O:17])[CH:14]2[CH2:13][CH2:12][CH2:11][CH2:10]3)=[O:8])=[CH:5][CH:4]=1.[NH:20]([CH2:24][CH2:25][OH:26])[CH2:21][CH2:22][OH:23].C(N(CC)C(C)C)(C)C.Cl>C(Cl)Cl>[OH:23][CH2:22][CH2:21][N:20]([CH2:24][CH2:25][OH:26])[C:15]([CH:14]1[CH2:13][CH2:12][CH2:11][CH2:10][C:9]1([OH:16])[C:7](=[O:8])[C:6]1[CH:18]=[CH:19][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:17]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8113DiethanolamineHCID 81531DiisopropylethylamineHCID 86629708HCID 86629708, compound

Product 1

HCID 57661209HCID 57661209, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 26.03 g (0.100 mol) of 6-(4-methoxy-benzoyl)-7-oxa-bicyclo[4.2.0]octan-8-one in 200 ml of methylene chloride is added to 10.5 g (0.100 mol) of diethanolamine and 32 ml of N,N-diisopropylethylamine. The reaction mixture is heated at reflux for several hours and monitored by thin layer chromatography. Upon completion of the reaction, the mixture is cooled and poured into 1N hydrochloric acid solution. The organic layer is washed with water, dried over anhydrous sodium sulfate, and concentrated to give the title compound.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureat reflux for several hours
  3. customUpon completion of the reaction
  4. temperaturethe mixture is cooled
  5. washThe organic layer is washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bdc8d13bf6834d5f8a0217d1e8a14ec6
Source dataset
uspto-grants-2013_02
Patent number
US08367743B2

Reaction notes

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