Triethylamine → HCID 86249861, compound

HRID 1665851Notes

Reaction equation

HRID 1665851 reaction equation
[OH:1][CH:2]([C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:4].C(N(CC)CC)C.[CH3:26][O:27][C:28](=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35](Cl)=[O:36]>C(Cl)Cl>[CH3:26][O:27][C:28](=[O:38])[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][C:35]([O:1][CH:2]([C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:3](=[O:4])[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1)=[O:36]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 4586585Methyl 8-chloro-8-oxooctanoateHCID 12505004HCID 12505004, compound

Product 1

HCID 86249861HCID 86249861, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 2-hydroxy-2-(4-methoxyphenyl)-1-phenyl-ethanone (8.2 g, 0.034 mol) prepared in Step 3 and triethylamine (5.21 g, 0.051 mol) in methylene chloride (100 mL) was slowly added a solution of 7-chlorocarbonylheptanoic acid methyl ester (5.64 g, 0.034 mol) in methylene chloride (20 mL). A final reaction solution was stirred at room temperature for 12 hours and then diluted with 200 mL of methylene chloride. The obtained organic layer was washed twice with 100 mL of a saturated sodium bicarbonate solution and then successively washed twice with 100 mL of a brine solution. The obtained organic layer was dried over magnesium sulfate, filtered and concentrated under reduced pressure, to give 12.90 g (yield: 92%) of octanedioic acid 1-(4-methoxyphenyl)-2-oxo-2-phenylethyl ester methyl ester.

Workup

  1. customA final reaction solution
  2. washThe obtained organic layer was washed twice with 100 mL of a saturated sodium bicarbonate solution
  3. washsuccessively washed twice with 100 mL of a brine solution
  4. dry with materialThe obtained organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-94967455352a4e7fb571485390507432
Source dataset
uspto-grants-2011_10
Patent number
US08039634B2

Reaction notes

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