Water → 2((4-(1-Oxo-3-carboxypropyl)-phenylthio)methyl)-3-propyl-4-hydroxy-5-acetyl-2,3-dihydrobenzo[b]furan

HRID 2290674Notes

Reaction equation

HRID 2290674 reaction equation
[O:1]=[C:2]([C:9]1[CH:14]=[CH:13][C:12]([S:15][CH2:16][CH:17]2[O:21][C:20]3[CH:22]=[CH:23][C:24]([C:27](=[O:29])[CH3:28])=[C:25]([OH:26])[C:19]=3[CH:18]2[CH2:30][CH2:31][CH3:32])=[CH:11][CH:10]=1)[CH2:3][CH2:4][C:5](=[O:8])[O:6]C.[OH-].[Na+].O>C1COCC1>[O:1]=[C:2]([C:9]1[CH:10]=[CH:11][C:12]([S:15][CH2:16][CH:17]2[O:21][C:20]3[CH:22]=[CH:23][C:24]([C:27](=[O:29])[CH3:28])=[C:25]([OH:26])[C:19]=3[CH:18]2[CH2:30][CH2:31][CH3:32])=[CH:13][CH:14]=1)[CH2:3][CH2:4][C:5]([OH:8])=[O:6]

Participants

5

Reactant 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 53886350HCID 53886350, compound

Product 1

HCID 137459452((4-(1-Oxo-3-carboxypropyl)-phenylthio)methyl)-3-propyl-4-hydroxy-5-acetyl-2,3-dihydrobenzo[b]furan

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The compound of Example 18 (430 mg, 0.9418 mmoles) was taken up in THF (5.8 ml) to which was added 1N NaOH (2.4 ml) and 2.5 ml H2O. The reaction mixture was stirred at room temperature under N2. After two hours, the THF was removed in vacuo and the reaction mixture was diluted to twice its volume with H2O and extracted with CHCl3. The aqueous phase was acidified with conc. HCl, extracted into CHCl3 and the organic phase was dried and concentrated. The residue was triturated with ether to afford the title compound, m.p. 110°-112°.

Workup

  1. customthe THF was removed in vacuo
  2. additionthe reaction mixture was diluted to twice its volume with H2O
  3. extractionextracted with CHCl3
  4. extractionextracted into CHCl3
  5. customthe organic phase was dried
  6. concentrationconcentrated
  7. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-d573dc04be9d4b6d859a1b90b89dfd7d
Source dataset
uspto-grants-1986_10
Patent number
US04617407

Reaction notes

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