Sodium Hydroxide → HCID 18427722, compound

HRID 2288168Notes

Reaction equation

HRID 2288168 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2[C:31]([O:33]C)=[O:32])=[C:5]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:4]=1.[OH-].[Na+]>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([O:18][CH2:19][CH2:20][CH3:21])[CH:16]=3)[CH:11]([C:22]3[CH:27]=[CH:26][C:25]4[O:28][CH2:29][O:30][C:24]=4[CH:23]=3)[CH:10]2[C:31]([OH:33])=[O:32])=[C:5]([C:35]2[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 18969640HCID 18969640, compound

Product 1

HCID 18427722HCID 18427722, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of Methyl (1RS,2RS,3RS)-3-(4-Methoxy-2-phenylphenyl)-1-(3,4-methylenedioxyphenyl)-5-(prop-1-yloxy)indane-2-carboxylate (80 mg, 0.12 mmol) in dioxane (2 mL) was added 1 M aqueous NaOH (0.3 mL, 0.3 mmol). The resulting mixture was heated to reflux for 48 h, then 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 residue purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane containing 5% of acetic acid) to afford the title compound (36 mg, 46%). m.p. 199-200° C.

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 48 h
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was partitioned between dilute aqueous HCl and ethyl acetate
  5. extractionThe ethyl acetate extract
  6. washwas washed with water
  7. dry with materialdried (MgSO4 anhydrous)
  8. customThe solvent was removed in vacuo
  9. customthe residue purified by flash column chromatography (silica gel, 20% ethyl acetate/hexane containing 5% of acetic acid)

Sources & evidence

ORD record
ord-a9027b2d4a524379923b377de6f42edb
Source dataset
uspto-grants-2000_07
Patent number
US06087389

Reaction notes

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