Potassium Carbonate → HCID 53806960, compound

HRID 745295Notes

Reaction equation

HRID 745295 reaction equation
[CH:1](=[C:8]1[C:12]2[O:13][C:14]3[CH:21]=[C:20]([OH:22])[CH:19]=[CH:18][C:15]=3[C:16](=[O:17])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl[CH2:24][CH2:25][N:26]1[CH2:31][CH2:30][O:29][CH2:28][CH2:27]1.C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[CH:1](=[C:8]1[C:12]2[O:13][C:14]3[CH:21]=[C:20]([O:22][CH2:24][CH2:25][N:26]4[CH2:31][CH2:30][O:29][CH2:28][CH2:27]4)[CH:19]=[CH:18][C:15]=3[C:16](=[O:17])[C:11]=2[CH2:10][CH2:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 767274-(2-Chloroethyl)morpholineHCID 54325690HCID 54325690, compound

Product 1

HCID 53806960HCID 53806960, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-Benzylidene-6-hydroxy-1,2,3,9-tetrahydro-cyclopenta[b][1]benzopyran-9-one (1.2 g) was reacted with 4-(2-chloro-ethyl)-morpholine (1.15 g) in dimethylformamide (50 ml), in the presence of anhydrous K2CO3 (1.7 g), under stirring for 4 hours at room temperature and then for 1 hour at 70° C. The reaction mixture was diluted with ice water containing NaH2PO4 and the precipitated product was filtered and washed with water. Crystallization from CH2Cl2 /isopropyl alcohol gave 0.9 g of 3-benzylidene-6-(2-morpholino-ethoxy)-1,2,3,9-tetrahydro-cyclopenta[b][1]benzopyran-9-one, m.p. 167°-169° C.

Workup

  1. waitfor 1 hour at 70° C
  2. filtrationthe precipitated product was filtered
  3. washwashed with water
  4. customCrystallization from CH2Cl2 /isopropyl alcohol

Sources & evidence

ORD record
ord-14ecdd753d134d6e9d9bd795eb434790
Source dataset
uspto-grants-1986_07
Patent number
US04598090

Reaction notes

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