Potassium Carbonate → HCID 69899609, compound

HRID 460663Notes

Reaction equation

HRID 460663 reaction equation
C(=O)([O-])[O-].[K+].[K+].[OH:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH:10]=[C:11]1[CH2:16][CH:15]([CH3:17])[O:14][C:12]1=[O:13].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:26][C@H:27]1[O:29][CH2:28]1)(=O)=O.[CH:39]1[C:48]2[C:43](=[CH:44][CH:45]=[CH:46][CH:47]=2)[CH:42]=[CH:41][C:40]=1[CH:49]1[CH2:54][CH2:53][NH:52][CH2:51][CH2:50]1>CO.CN(C)C=O>[OH:29][CH:27]([CH2:28][N:52]1[CH2:53][CH2:54][CH:49]([C:40]2[CH:41]=[CH:42][C:43]3[C:48](=[CH:47][CH:46]=[CH:45][CH:44]=3)[CH:39]=2)[CH2:50][CH2:51]1)[CH2:26][O:7][C:8]1[CH:21]=[CH:20][CH:19]=[CH:18][C:9]=1[CH:10]=[C:11]1[CH2:16][C@H:15]([CH3:17])[O:14][C:12]1=[O:13]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 10868995(S)-(+)-Glycidyl-4-nitrobenzoateHCID 220292644-(Naphthalen-2-yl)piperidineHCID 69497707alpha-(2'-Hydroxybenzylidene)-gamma-valerolactone

Product 1

HCID 69899609HCID 69899609, compoundYield 35.8%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
40 °C

Procedure

Dimethylformamide (70 ml) and potassium carbonate (9.5 g) were added to α-(2′-hydroxybenzylidene)-γ-valerolactone (7 g) and (S)-glycidyl nosylate (8.9 g) was added. The mixture was stirred at 40° C. for 2 hr. The reaction mixture was concentrated under reduced pressure. Water was added and the mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate and concentrated under reduced pressure to give an oil. (7.5 g). By the reaction using this product (1.0 g) and 4-(naphthalen-2-yl)piperidine (1.0 g) in methanol (50 ml) in the same manner as in Example 307, an oily title compound (0.8 g) was obtained.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionWater was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give an oil

Sources & evidence

ORD record
ord-4ae790f7ff824addb25d9460b973d4e9
Source dataset
uspto-grants-2007_03
Patent number
US07196199B2

Reaction notes

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