Dimethyl Sulfoxide → 1-[2-(2,2-Dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]-3,3-dimethylbutan-2-one

HRID 2103774Notes

Reaction equation

HRID 2103774 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([C:31]([CH3:34])([CH3:33])[CH3:32])[CH2:13][C:14]1[C:18]2[CH:19]=[C:20]([O:23][CH3:24])[CH:21]=[CH:22][C:17]=2[O:16][C:15]=1[C:25](=[O:30])[C:26]([CH3:29])([CH3:28])[CH3:27].C(N(CC)CC)C>C(=O)=O.ClCCl>[CH3:27][C:26]([CH3:29])([CH3:28])[C:25]([C:15]1[O:16][C:17]2[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=2[C:14]=1[CH2:13][C:12](=[O:11])[C:31]([CH3:32])([CH3:33])[CH3:34])=[O:30]

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 578044731-[3-(2-Hydroxy-3,3-dimethylbutyl)-5-methoxy-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one

Product 1

HCID 113594461-[2-(2,2-Dimethylpropanoyl)-5-methoxy-1-benzofuran-3-yl]-3,3-dimethylbutan-2-one

Reagents, catalysts & solvents 2

HCID 280Carbon DioxideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Cool 1.5 mL dichloromethane in dry ice bath under nitrogen. Add 38 mg oxalyl chloride followed by 47 mg DMSO. Stir for 30 minutes. Add a solution of 49.9 mg 1-[3-(2-hydroxy-3,3-dimethylbutyl)-5-methoxy-1-benzofuran-2-yl]-2,2-dimethylpropan-1-one from the Step A above in 2.5 mL dichloromethane. After another 25 minutes, 167 μL triethylamine were added. After stirring for additional 25 minutes, the reaction mixture was removed from the cooling bath and allowed to warm to room temperature. After 2 hours, solvents were removed under reduced pressure and the residue was purified directly on RP-HPLC using 70-100% MeCN gradient. The fractions containing pure product were pooled and lyophilized to give the title compound. 1H NMR (CDCl3, 500 MHz) 7.43 (d, J=8.9 Hz, 1H), 7.10 (dd, J=2.5 & 8.9 Hz, 1H), 6.90 (d, J=2.6 Hz, 1H), 4.39 (s, 2H), 3.87 (s, 3H), 1.42 (s, 9H), 1.34 (s, 9H). LC-MS: 4.17 min. (m/Z=247.2, 353.3, 331.4).

Workup

  1. waitAfter another 25 minutes
  2. stirringAfter stirring for additional 25 minutes
  3. customthe reaction mixture was removed from the cooling bath
  4. waitAfter 2 hours
  5. customsolvents were removed under reduced pressure
  6. customthe residue was purified directly on RP-HPLC using 70-100% MeCN gradient
  7. additionThe fractions containing pure product

Sources & evidence

ORD record
ord-dff99023dc1e4804a5c604e4adcc6edd
Source dataset
uspto-grants-2009_08
Patent number
US07576122B2

Reaction notes

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