Dichloromethane → 3-Benzo[1,3]dioxol-5-yl-5-(3-dimethylamino-propoxy)-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

HRID 367034Notes

Reaction equation

HRID 367034 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11](=[O:37])[O:12][C:13]([OH:36])([C:28]4[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=4)[C:14]=3[CH2:15][C:16]3[CH:21]=[C:20]([O:22][CH3:23])[C:19]([O:24][CH3:25])=[C:18]([O:26][CH3:27])[CH:17]=3)=[CH:9][C:4]=2[O:3][CH2:2]1.OC[CH2:40][N:41]1[CH2:46][CH2:45]OC[CH2:42]1.Cl[CH2:48]Cl>>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([C:10]3[C:11](=[O:37])[O:12][C:13]([O:36][CH2:48][CH2:45][CH2:46][N:41]([CH3:42])[CH3:40])([C:28]4[CH:29]=[CH:30][C:31]([O:34][CH3:35])=[CH:32][CH:33]=4)[C:14]=3[CH2:15][C:16]3[CH:17]=[C:18]([O:26][CH3:27])[C:19]([O:24][CH3:25])=[C:20]([O:22][CH3:23])[CH:21]=3)=[CH:9][C:4]=2[O:3][CH2:2]1

Participants

4

Reactant 3

HCID 6344DichloromethaneHCID 611632-Morpholinoethanol2×HCID 9870830CI 1020

Product 1

HCID 158955133-Benzo[1,3]dioxol-5-yl-5-(3-dimethylamino-propoxy)-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

Procedure

To 125 mL dichloromethane was added 3-Benzo[1,3]-dioxol-5-yl-5-hydroxy-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one 6.06 g (11.96 mmol), giving a suspension. 4-(2-Hydroxyethyl)morpholine 3 g (22.86 imol) was added, and the mixture was purged with anhydrous HCl gas until saturated. After 3 hours at room temperature, additional 4-(2-hydroxyethyl)-morphline 3 g (22.86 mmol) was added, followed by stirring for 24 hours at room temperature. The mixture was evaporated in vacuo, and the residue was suspended in ethyl ether. The ether suspension was washed exhaustively with 4 N NaOH, followed by water and saturated sodium chloride solution. The ether phase was dried over anhydrous magnesium sulfate, filtered, and evaporated in vacuo to a crude foam, 2.86 g. The crude material was purified by chromatography on 200 g silica gel eluted with 5% methanol in chloroform. The appropriate fractions were evaporated to a glassy solid, 2.0 g. The product was identified by 1H NMR, MS [M--H]+ =620 Da.

Workup

  1. customgiving a suspension
  2. customthe mixture was purged with anhydrous HCl gas until saturated
  3. customThe mixture was evaporated in vacuo
  4. washThe ether suspension was washed exhaustively with 4 N NaOH
  5. dry with materialThe ether phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. customevaporated in vacuo to a crude foam, 2.86 g
  8. customThe crude material was purified by chromatography on 200 g silica gel
  9. washeluted with 5% methanol in chloroform
  10. customThe appropriate fractions were evaporated to a glassy solid, 2.0 g

Sources & evidence

ORD record
ord-33e7f8c9f17f470e8b11ec46b4efdb1d
Source dataset
uspto-grants-2000_10
Patent number
US06133263

Reaction notes

Loading…