Sodium Hydroxide → HCID 44211033, compound

HRID 2288169Notes

Reaction equation

HRID 2288169 reaction equation
[C:1](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH3:27])[CH:22]=2)[CH:17]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[CH:16]1[C:37]([O:39]C)=[O:38])([O:3]C)=[O:2].[OH-].[Na+]>O1CCOCC1>[C:1](/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[CH:10]=[CH:9][C:8]=1[CH:15]1[C:23]2[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][CH2:26][CH3:27])[CH:22]=2)[CH:17]([C:28]2[CH:33]=[CH:32][C:31]3[O:34][CH2:35][O:36][C:30]=3[CH:29]=2)[CH:16]1[C:37]([OH:39])=[O:38])([OH:3])=[O:2]

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 67643205HCID 67643205, compound

Product 1

HCID 44211033HCID 44211033, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of methyl (1RS,2SR,3SR)-3-[2-[(E)-2-carbomethoxyethen-1-yl]-4-methoxyphenyl]-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (80 mg, 0.15 mmol) in dioxane (2 ml) was added 1 N NaOH (0.5 ml, 0.5 mmol). The resulting mixture was heated to reflux for 3 h, then cooled and concentrated under reduced pressure. The residue was partitioned between dilute aqueous HCl and ethyl acetate. The ethyl acetate extract was washed with water and dried (MgSO4 anhydrous). The solvent was removed in vacuo and the title compound was obtained as a white solid (73 mg, 96%).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 3 h
  3. temperaturecooled
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was partitioned between dilute aqueous HCl and ethyl acetate
  6. extractionThe ethyl acetate extract
  7. washwas washed with water
  8. dry with materialdried (MgSO4 anhydrous)
  9. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-cdb74b4c8d464612ad8ad1cd35a223b5
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

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