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

HRID 367035Notes

Reaction equation

HRID 367035 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.[Br:38][CH2:39][CH2:40][CH2:41]O>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][CH2:41][CH2:40][CH2:39][Br: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

4

Reactant 2

HCID 123083-Bromo-1-propanolHCID 9870830CI 1020

Product 1

HCID 158955113-Benzo[1,3]dioxol-5-yl-5-(3-bromo-propoxy)-5-(4-methoxy-phenyl)-4-(3,4,5-trimethoxy-benzyl)-5H-furan-2-one

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 100 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 5.0 g (9.87 mmol), giving a suspension. 1-Bromo-3-propanol 3.07 g (22.15 mmol) was added, and the mixture was purged with anhydrous HCl gas until saturated. After 48 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 0.5 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, 4.79 g. The product was identified by 1H NMR, MS [M--H]+ =628, 629 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 0.5 N NaOH
  5. dry with materialThe ether phase was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. additiondiluted with hexane
  8. customgiving a solid
  9. filtrationFilter
  10. customdry in vacuo
  11. customgiving a white solid, 4.79 g

Sources & evidence

ORD record
ord-054b68463cf34f8a97161f009bfd12a6
Source dataset
uspto-grants-2000_10
Patent number
US06133263

Reaction notes

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