Dimethylformamide → alpha-(2'-(2,3-Epoxypropan-1-yloxy)benzylidene)-gamma-butyrolactone

HRID 460658Notes

Reaction equation

CN(C)C=O.C(=O)([O-])[O-].[K+].[K+].[OH:12][C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[CH:15]=[C:16]1[CH2:21][CH2:20][O:19][C:17]1=[O:18].S(C1C=CC([N+]([O-])=O)=CC=1)(O[CH2:30][CH:31]1[O:33][CH2:32]1)(=O)=O>O>[O:33]1[CH2:32][CH:31]1[CH2:30][O:12][C:13]1[CH:25]=[CH:24][CH:23]=[CH:22][C:14]=1[CH:15]=[C:16]1[CH2:21][CH2:20][O:19][C:17]1=[O:18]

Participants

Conditions

Temperature: 50 °C

Procedure

Dimethylformamide (30 ml) and potassium carbonate (4.4 g) were added to α-(2′-hydroxybenzylidene)-γ-butyrolactone (3 g), and a racemic compound of glycidyl nosylate (3.4 g) was added. The mixture was stirred at 50° C. for 3 hr. 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 oily α-(2′-(2,3-epoxypropan-1-yloxy)benzylidene)-γ-butyrolactone (3.2 g). This compound (0.4 g) was reacted in methanol with 4-(naphthalen-2-yl)piperidine (0.5 g) in the same manner as in Example 307 to give the title compound, melting point 127–128° C.

Workup

extractionthe mixture was extracted with ethyl acetate
dry with materialThe organic layer was dried over anhydrous sodium sulfate
concentrationconcentrated under reduced pressure

Sources & evidence

ORD record: ord-b4fe74838dec4c33a54134100278b4aa
Source dataset: uspto-grants-2007_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07196199B2

Reaction notes

Loading…