2-(Dimethylamino)ethanol → 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 367037Notes

Reaction equation

HRID 367037 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.[CH3:38][N:39]([CH2:41][CH2:42][CH2:43]O)[CH3:40].CN(C)CCO>ClCCl>[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][CH2:43][CH2:42][CH2:41][N:39]([CH3:40])[CH3:38])([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

5

Reactant 3

HCID 79022-(Dimethylamino)ethanolHCID 766463-(Dimethylamino)-1-propanolHCID 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

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

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 3.0 g (5.92 mmol), giving a suspension. N,N-dimethyl-propanolamine 2 g (19.4 mmol) was added, and the mixture was purged with anhydrous HCl gas until saturated. After an hour at room temperature, additional N,N-dimethylethanolamine 1 g (9.69 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 diluted with hexane, giving a solid. Filter and dry in vacuo, giving a white solid, 1.65 g. The product was identified by 1H NMR, MS [M--H]+ =592 Da.

Workup

  1. customgiving a suspension
  2. customthe mixture was purged with anhydrous HCl gas until saturated
  3. waitAfter an hour at room temperature
  4. customThe mixture was evaporated in vacuo
  5. washThe ether suspension was washed exhaustively with 4 N NaOH
  6. dry with materialThe ether phase was dried over anhydrous magnesium sulfate
  7. filtrationfiltered
  8. additiondiluted with hexane
  9. customgiving a solid
  10. filtrationFilter
  11. customdry in vacuo
  12. customgiving a white solid, 1.65 g

Sources & evidence

ORD record
ord-48bc46e5c976426d83a91baa555fd1a8
Source dataset
uspto-grants-2000_10
Patent number
US06133263

Reaction notes

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