Sodium ethoxide → HCID 59692835, compound

HRID 898840Notes

Reaction equation

HRID 898840 reaction equation
[O-]CC.[Na+].C1(C)C=CC(S([O-])(=O)=O)=CC=1.[CH2:16]([O:18][C:19]([CH:21]([C:35]([O:37][CH2:38][CH3:39])=[O:36])[C:22]([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)([CH3:27])[CH2:23][S+](C)C)=[O:20])[CH3:17]>C(O)C>[CH2:16]([O:18][C:19]([C:21]1([C:35]([O:37][CH2:38][CH3:39])=[O:36])[CH2:23][C:22]1([C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][CH:29]=1)[CH3:27])=[O:20])[CH3:17]

Participants

4

Reactant 2

HCID 2723922Sodium ethoxideHCID 86607495HCID 86607495, compound

Product 1

HCID 59692835HCID 59692835, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Under ice-cooling and under nitrogen atmosphere, a solution of 21% sodium ethoxide in ethanol (1.6 mL, 4.4 mmol) was added to a solution of the crude product (2.9 mmol) of [3,3-bis-ethoxycarbonyl-2-(4-fluorophenyl)-2-methylpropyl]dimethylsulfonium p-toluenesulfonate in ethanol (10 mL), which was obtained in Preparation Example 1-5, and the mixture was stirred for 1 hour. The obtained solution was concentrated under reduced pressure, and the residue was neutralized by the addition of a 2N aqueous hydrochloric acid solution, and the aqueous layer was extracted with ethyl acetate (10 mL). The organic layer was dried over magnesium sulfate and filtrated, and the solvent was evaporated. Then, the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=20:1 to 5:1) to give the title compound (0.64 g, yield 75%) as a pale-yellow oil.

Workup

  1. temperatureUnder ice-cooling and under nitrogen atmosphere
  2. customwhich was obtained in Preparation Example 1-5
  3. concentrationThe obtained solution was concentrated under reduced pressure
  4. additionthe residue was neutralized by the addition of a 2N aqueous hydrochloric acid solution
  5. extractionthe aqueous layer was extracted with ethyl acetate (10 mL)
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltrated
  8. customthe solvent was evaporated
  9. customThen, the obtained residue was purified by silica gel chromatography (hexane:ethyl acetate=20:1 to 5:1)

Sources & evidence

ORD record
ord-ede7e31cba484ce1a3289ded79e5e062
Source dataset
uspto-grants-2008_04
Patent number
US07351825B2

Reaction notes

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