Tetrahydrofuran → HCID 12043169, compound

HRID 2184763Notes

Reaction equation

HRID 2184763 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:12]=[CH:11][C:10]([C:13](=[O:20])[CH2:14][CH2:15][C:16]([O:18]C)=[O:17])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[OH-].[Na+].O1CCCC1>CO>[Cl:1][C:2]1[S:6][C:5]([C:7]2[CH:8]=[CH:9][C:10]([C:13](=[O:20])[CH2:14][CH2:15][C:16]([OH:18])=[O:17])=[CH:11][CH:12]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 86758103HCID 86758103, compound

Product 1

HCID 12043169HCID 12043169, compoundYield 52.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4-[4-(5-chloro-thiophen-2-yl)-phenyl]-4-oxo-butyric acid, methyl ester (5.99 g, 0.0194 mol), 1.0 M aqueous sodium hydroxide (23 mL, 0.023 mol), tetrahydrofuran (50 mL), and methanol (50 mL) was stirred at room temperature for 26 hours. The resulting suspension was filtered, and the filtercake was washed with methanol. The filtercake was partitioned between dichloromethane-tetrahydrofuran-ethyl acetate (100 mL each) and 0.5 M aqueous hydrochloric acid (50 mL). The organics were washed with brine, dried (Na2SO4), and rotary evaporated to give 2.99 g of 4-[4-(5-chloro-thiophen-2-yl)-phenyl]-4-oxo-butyric acid as a bright yellow solid; mp 212-213° C.

Workup

  1. filtrationThe resulting suspension was filtered
  2. washthe filtercake was washed with methanol
  3. customThe filtercake was partitioned between dichloromethane-tetrahydrofuran-ethyl acetate (100 mL each) and 0.5 M aqueous hydrochloric acid (50 mL)
  4. washThe organics were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customrotary evaporated

Sources & evidence

ORD record
ord-06d3d0b5a80c4028996c14fb298f3fe5
Source dataset
uspto-grants-2002_06
Patent number
US06399612B1

Reaction notes

Loading…