Triethylamine → HCID 58079329, compound

HRID 1027373Notes

Reaction equation

HRID 1027373 reaction equation
[CH3:1][C:2]([CH3:7])([CH3:6])[C:3](Cl)=[O:4].[CH3:8][C:9]1[CH:14]=[C:13]([CH3:15])[CH:12]=[C:11]([CH3:16])[C:10]=1[CH:17]1[C:22](=[O:23])[CH2:21][CH:20]([CH2:24][CH:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[CH2:19][C:18]1=[O:30].C(N(CC)CC)C>ClCCl>[O:23]=[C:22]1[CH2:21][CH:20]([CH2:24][CH:25]2[CH2:29][CH2:28][O:27][CH2:26]2)[CH2:19][C:18]([O:30][C:3](=[O:4])[C:2]([CH3:7])([CH3:6])[CH3:1])=[C:17]1[C:10]1[C:11]([CH3:16])=[CH:12][C:13]([CH3:15])=[CH:14][C:9]=1[CH3:8]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 66724946HCID 66724946, compound

Product 1

HCID 58079329HCID 58079329, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Conditions

Temperature
0 °C

Procedure

A solution of trimethylacetyl chloride (55 mg, 0.457 mmol) in dichloromethane (2 ml) is added dropwise to a solution of 2-(2,4,6-trimethylphenyl)-5-(tetrahydrofuran-3-ylmethyl)-cyclohexane-1,3-dione (120 mg, 0.38 mmol) in dichloromethane (2 ml) and the mixture is cooled in an ice bath and stirred at 0° C. for 2 minutes. A solution of triethylamine (46 mgs, 0.457 mmol) in dichloromethane (1 ml) is added, and once the addition is complete the cooling bath is removed and the reaction mixture is stirred at room temperature for 2 hours. The mixture is diluted with dichloromethane (20 ml) and washed with saturated aqueous sodium bicarbonate solution (3×20 ml). The organic phase is dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated in vacuo. The residue is purified by column chromatography on silica gel to give 2,2-dimethylpropionic acid 3-oxo-5-(tetrahydrofuran-3-ylmethyl)-2-(2,4,6-trimethylphenyl)cyclohex-1-enyl ester as a white solid, m.p. 108-110° C.

Workup

  1. temperaturethe mixture is cooled in an ice bath
  2. additiononce the addition
  3. customis removed
  4. stirringthe reaction mixture is stirred at room temperature for 2 hours
  5. additionThe mixture is diluted with dichloromethane (20 ml)
  6. washwashed with saturated aqueous sodium bicarbonate solution (3×20 ml)
  7. dry with materialThe organic phase is dried over anhydrous magnesium sulfate
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe residue is purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-4f9930580be64e7ebc589ccaf784b561
Source dataset
uspto-grants-2014_05
Patent number
US08735322B2

Reaction notes

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