Triethylamine → Rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester

HRID 514203Notes

Reaction equation

HRID 514203 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([CH:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]2=[O:22])=[C:4]([CH3:23])[CH:3]=1.C(N(CC)CC)C.[C:31](Cl)(=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33]>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([CH3:23])[C:5]([C:9]2[C:13](=[O:14])[CH:12]([CH2:15][CH:16]3[CH2:21][CH2:20][O:19][CH2:18][CH2:17]3)[CH2:11][C:10]=2[O:22][C:31](=[O:36])[C:32]([CH3:35])([CH3:34])[CH3:33])=[C:6]([CH3:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62493Pivaloyl chlorideHCID 58481464HCID 58481464, compound

Product 1

HCID 58481557Rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of rac-2-(4-bromo-2,6-dimethylphenyl)-4-(tetrahydropyran-4-ylmethyl)cyclopentane-1,3-dione (1.0 g, 2.6 mmol) in dichloromethane (20 ml) is added triethylamine (1.09 ml, 7.8 mmol) then pivaloyl chloride (1.10 ml, 7.8 mmol), and the resulting solution is stirred at room temperature for 4 hours. The reaction mixture is diluted with dichloromethane (100 ml), washed with distilled water (50 ml×3), and the organic fractions are combined, dried over sodium sulphate, filtered and the filtrate concentrated in vacuo to afford rac-2,2-dimethylpropionic acid 2-(4-bromo-2,6-dimethylphenyl)-3-oxo-4-(tetrahydropyran-4-ylmethyl)cyclopent-1-enyl ester. This material is used directly in the next step without further purification.

Workup

  1. washwashed with distilled water (50 ml×3)
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated in vacuo

Sources & evidence

ORD record
ord-dc770d7818e142008dd833183a633a5f
Source dataset
uspto-grants-2015_08
Patent number
US09107415B2

Reaction notes

Loading…