Sodium Bicarbonate → Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

HRID 1516707Notes

Reaction equation

HRID 1516707 reaction equation
Br[Mg][C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=1.[C:13]1([C:18]2[C:27]([CH:28]=[O:29])=[C:26]([CH:30]([CH3:32])[CH3:31])[CH:25]=[C:24]3[C:19]=2[C:20](=[O:35])[CH2:21][C:22]([CH3:34])([CH3:33])[O:23]3)[CH2:17][CH2:16][CH2:15][CH:14]=1.C(=O)(O)[O-].[Na+]>O1CCCC1>[C:13]1([C:18]2[C:27]([CH:28]([OH:29])[C:3]3[CH:8]=[CH:7][C:6]([C:9]([F:12])([F:11])[F:10])=[CH:5][CH:4]=3)=[C:26]([CH:30]([CH3:31])[CH3:32])[CH:25]=[C:24]3[C:19]=2[C:20](=[O:35])[CH2:21][C:22]([CH3:33])([CH3:34])[O:23]3)[CH2:17][CH2:16][CH2:15][CH:14]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 580029585-Cyclopent-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehydeHCID 178506198HCID 178506198, compound

Product 1

HCID 58002986Rac-5-cyclopent-1-en-1-yl-6-{hydroxy[4-(trifluoromethyl)phenyl]methyl}-7-isopropyl-2,2-dimethyl-2,3-dihydro-4h-chromen-4-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

At −78° C., 780 μl (391 μmol) of a freshly prepared 0.5 M solution of bromo[4-(trifluoromethyl)phenyl]magnesium in tetrahydrofuran are slowly added dropwise to a solution of 94 mg (301 μmol) of 5-cyclopent-1-en-1-yl-7-isopropyl-2,2-dimethyl-4-oxochroman-6-carbaldehyde (Example 34A) in 2.3 ml of tetrahydrofuran. The mixture is then allowed to thaw slowly to −20° C. and stirred at this temperature for 45 min. 10% strength sodium bicarbonate solution is then added, the mixture is extracted three times with ethyl acetate and the combined organic phases are washed with saturated sodium chloride solution. The organic phases are dried over magnesium sulfate, the solvent is removed under reduced pressure and the residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 20:1→10:1) and then by preparative HPLC (method 1).

Workup

  1. customthaw slowly to −20° C.
  2. extractionthe mixture is extracted three times with ethyl acetate
  3. washthe combined organic phases are washed with saturated sodium chloride solution
  4. dry with materialThe organic phases are dried over magnesium sulfate
  5. customthe solvent is removed under reduced pressure
  6. customthe residue is purified by column chromatography on silica gel (mobile phase: gradient cyclohexane→cyclohexane/ethyl acetate 20:1→10:1)

Sources & evidence

ORD record
ord-cdab02487d0046d0b5f4a23a8b725ee3
Source dataset
uspto-grants-2012_07
Patent number
US08227511B2

Reaction notes

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