Sodium Hydroxide → HCID 44211033, compound

HRID 650417Notes

Reaction equation

HRID 650417 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])=[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 86584129HCID 86584129, 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-b033924e6ac9484eb3e3d0fa34c5439d
Source dataset
uspto-grants-2001_08
Patent number
US06271399B1

Reaction notes

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