Sodium Hydroxide → HCID 69177739, compound

HRID 899790Notes

Reaction equation

HRID 899790 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=[O:11])[N:3]1[CH2:12][CH2:13][C:14](=[CH2:25])[CH2:15][O:16]C(=O)C1C=CC=CC=1.[O:26]=[C:27]1[C:35]2[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:29](=[O:36])[N:28]1[CH2:37][C:38](=[CH2:50])[CH2:39][CH2:40][O:41]C(=O)C1C=CC=CC=1.[OH-].[Na+]>CO.C(OCC)(=O)C.C([O-])(O)=O.[Na+]>[OH:16][CH2:15][C:14](=[CH2:25])[CH2:13][CH2:12][N:3]1[C:4](=[O:11])[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[C:2]1=[O:1].[OH:41][CH2:40][CH2:39][C:38](=[CH2:50])[CH2:37][N:28]1[C:29](=[O:36])[C:30]2[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:27]1=[O:26]

Participants

8

Reactant 3

HCID 14798Sodium HydroxideHCID 86590312HCID 86590312, compoundHCID 86590313HCID 86590313, compound

Product 2

HCID 69157686HCID 69157686, compoundYield 7%HCID 69177739HCID 69177739, compoundYield 29%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolventHCID 516892Sodium BicarbonateSolvent

Procedure

To an ˜3:1 mixture of benzoic acid 4-(1,3-dioxo-1,3-dihydro-isoindol-2-yl)-2-methylene-butyl ester and benzoic acid 3-(1,3-dioxo-1,3-dihydro-isoindol-2-ylmethyl)-but-3-enyl ester (4.11 g, 12.3 mmol) in methanol (123 mL) was added NaOH (1.21 g, 30.3 mmol) and the mixture was stirred at room temperature for 30 minutes. The mixture was diluted with ethyl acetate (250 mL) and saturated aqueous NaHCO3 (125 mL). The phases were separated and the aqueous phase was extracted with ethyl acetate (3×100 mL). The combined organic extracts were washed with brine (3×30 mL), dried (MgSO4), and concentrated. Purification of the crude material by column chromatography on silica gel (2:1 hexanes-ethyl acetate) provided 0.83 g (29%) of 2-(3-Hydroxymethyl-but-3-enyl)-isoindole-1,3-dione as a white solid and 0.19 g (7%) of 2-(4-Hydroxy-2-methylene-butyl)-isoindole-1,3-dione as a white solid.

Workup

  1. customThe phases were separated
  2. extractionthe aqueous phase was extracted with ethyl acetate (3×100 mL)
  3. washThe combined organic extracts were washed with brine (3×30 mL)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customPurification of the crude material by column chromatography on silica gel (2:1 hexanes-ethyl acetate)

Sources & evidence

ORD record
ord-678b0ed703a644509f4b71b71cd289c3
Source dataset
uspto-grants-2008_04
Patent number
US07354934B2

Reaction notes

Loading…