Triethylamine → HCID 66868360, compound

HRID 1631893Notes

Reaction equation

HRID 1631893 reaction equation
[CH:1]1([CH:4](O)[CH:5]2[C:9](=[O:10])[C:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:7]([O:20][CH3:21])[CH2:6]2)[CH2:3][CH2:2]1.CCN(CC)CC.CS(Cl)(=O)=O.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl>[CH:1]1([CH:4]=[C:5]2[C:9](=[O:10])[C:8]([C:11]3[C:16]([CH3:17])=[CH:15][C:14]([CH3:18])=[CH:13][C:12]=3[CH3:19])=[C:7]([O:20][CH3:21])[CH2:6]2)[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11430Potassium CarbonateHCID 31297Methanesulfonyl chlorideHCID 66868045HCID 66868045, compound

Product 1

HCID 66868360HCID 66868360, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(Cyclopropyl-hydroxy-methyl)-3-methoxy-2-(2,4,6-trimethyl-phenyl)-cyclopent-2-enone (622 mg, 2.1 mmol) in CH2Cl2 (10 ml) at 0 C were added dropwise Et3N (0.59 ml, 4.2 mmol) followed my methane sulfonyl chloride (0.33 ml, 4.2 mmol). The reaction was allowed to warm to room temperature over 10 minutes and then quenched by addition of 1M HCl (10 ml). The layers were separated and the organic phase was evaporated to dryness under reduced pressure. The crude mesylate was dissolved in MeOH (10 ml) and K2CO3 (580 mg, 4.2 mmol) was added in a single portion. The reaction was stirred at room temperature for 2 hours and then the solvent was removed under reduced pressure. The crude material was partitioned between EtOAc (20 ml) and H2O (20 ml), the organic phase was washed with brine (20 ml), dried over MgSO4, filtered and evaporated to dryness under reduced pressure. The crude material was purified by flash chromatography over SiO2 using a 100% isohexane to 100% EtOAc gradient to give the desired product as a colourless oil (83 mg).

Workup

  1. customquenched by addition of 1M HCl (10 ml)
  2. customThe layers were separated
  3. customthe organic phase was evaporated to dryness under reduced pressure
  4. dissolutionThe crude mesylate was dissolved in MeOH (10 ml)
  5. customthe solvent was removed under reduced pressure
  6. customThe crude material was partitioned between EtOAc (20 ml) and H2O (20 ml)
  7. washthe organic phase was washed with brine (20 ml)
  8. dry with materialdried over MgSO4
  9. filtrationfiltered
  10. customevaporated to dryness under reduced pressure
  11. customThe crude material was purified by flash chromatography over SiO2 using a 100% isohexane to 100% EtOAc gradient

Sources & evidence

ORD record
ord-707bf2d2825a4ee5b03a4f04717b6e7b
Source dataset
uspto-grants-2014_07
Patent number
US08791303B2

Reaction notes

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