Hydrochloric Acid → HCID 11186494, compound

HRID 603326Notes

Reaction equation

HRID 603326 reaction equation
[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][S:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([O:17]CC)=[O:16])=[CH:8][CH:7]=1.[OH-].[Na+].Cl>C(O)C>[CH3:1][C:2]1[CH:24]=[CH:23][CH:22]=[C:21]([CH3:25])[C:3]=1[CH2:4][S:5][C:6]1[CH:7]=[CH:8][C:9]([C:12](=[O:20])[CH2:13][CH2:14][C:15]([OH:17])=[O:16])=[CH:10][CH:11]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 67027335HCID 67027335, compound

Product 1

HCID 11186494HCID 11186494, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of Ethyl 4-(4-[(2,6-dimethylbenzyl)-thio]-phenyl)-4-oxobutyrate (Step D, 0.680 g, 2 mmol) in abs ethanol (20 ml) was treated with 1N NaOH (3 ml) at room temperature. The reaction mixture was stirred for 3 hours, acidified with 1M HCl and concentrated. The residue was taken in chloroform and washed with 0.1 M HCl, brine, dried over Na2SO4, filtered and concentrated. The purification was done by flash chromatography on a silica gel column (chloroform:methanol (95:5) spiked with acetic acid) to provide the title compound as off white solid.

Workup

  1. concentrationconcentrated
  2. washwashed with 0.1 M HCl, brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe purification

Sources & evidence

ORD record
ord-56ea3d1dc1c94ca6b5c473ea3d3100a1
Source dataset
uspto-grants-2011_03
Patent number
US07906675B2

Reaction notes

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