3-Furancarboxaldehyde, tetrahydro- → 2-(3,5-Dimethylbiphenyl-4-yl)-5-[hydroxyl-(tetrahydrofuran-3-yl)-methyl]-3-methoxy-cyclopent-2-enone

HRID 509162Notes

Reaction equation

HRID 509162 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=[C:6]([CH3:16])[C:7]=1[C:8]1[C:9](=[O:15])[CH2:10][CH2:11][C:12]=1[O:13][CH3:14].C[Si]([N-][Si](C)(C)C)(C)C.[Li+].[O:33]1[CH2:37][CH2:36][CH:35]([CH:38]=[O:39])[CH2:34]1>O1CCCC1>[CH3:16][C:6]1[CH:5]=[C:4]([C:17]2[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=2)[CH:3]=[C:2]([CH3:1])[C:7]=1[C:8]1[C:9](=[O:15])[CH:10]([CH:38]([OH:39])[CH:35]2[CH2:36][CH2:37][O:33][CH2:34]2)[CH2:11][C:12]=1[O:13][CH3:14]

Participants

5

Reactant 3

HCID 1575683-Furancarboxaldehyde, tetrahydro-HCID 2733832Lithium HexamethyldisilazideHCID 584815132-(3,5-Dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone

Product 1

HCID 584816012-(3,5-Dimethylbiphenyl-4-yl)-5-[hydroxyl-(tetrahydrofuran-3-yl)-methyl]-3-methoxy-cyclopent-2-enoneYield 136.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Conditions

Temperature
-75 °C

Procedure

To a solution of 2-(3,5-Dimethylbiphenyl-4-yl)-3-methoxy cyclopent-2-enone (0.6 g, 2.05 mmol) in tetrahydrofuran (12 ml) is added 1 molar solution of lithium bis(trimethylsilyl)amide in THF (2.5 ml, 2.5 mmol) under nitrogen atmosphere at −75° C. The resulting solution is stirred at −75° C. for 40 minutes and to this mixture, a solution of 3-tetrahydrofurancarboxaldehyde (0.42 g, 4.1 mmol) in THF is added over 20 minutes. The resulting solution is stirred at −75° C. for 2 hours. The cooling bath is removed and the mixture is allowed to reach room temperature, then stirred for 2 hours. The reaction mixture is quenched with ice cold water (100 ml) and extracted with ethyl acetate (3×75 ml, dried over anhydrous sodium sulphate, filtered and the filtrate is concentrated in vacuo to give a residue (1.1 g) which is used as such for the next step.

Workup

  1. stirringThe resulting solution is stirred at −75° C. for 2 hours
  2. customThe cooling bath is removed
  3. customto reach room temperature
  4. stirringstirred for 2 hours
  5. customThe reaction mixture is quenched with ice cold water (100 ml)
  6. extractionextracted with ethyl acetate (3×75 ml
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationthe filtrate is concentrated in vacuo

Sources & evidence

ORD record
ord-931feb6007b5430ebf121964a506e4f2
Source dataset
uspto-grants-2015_08
Patent number
US09096560B2

Reaction notes

Loading…