Methanol → 2-[(5-Chlorothiophen-2-yl)oxy]acetic acid

HRID 1432880Notes

Reaction equation

HRID 1432880 reaction equation
[Cl:1][C:2]1[S:6][C:5]([O:7][CH2:8][C:9]([O:11]CC)=[O:10])=[CH:4][CH:3]=1.CO.C1COCC1.[Li+].[OH-]>O>[Cl:1][C:2]1[S:6][C:5]([O:7][CH2:8][C:9]([OH:11])=[O:10])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 3939Lithium HydroxideHCID 8028TetrahydrofuranHCID 9964518HCID 9964518, compound

Product 1

HCID 111831442-[(5-Chlorothiophen-2-yl)oxy]acetic acidYield 93.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of ethyl 5-chloro-2-thienyloxyacetate (0.39 g, 1.77 mmol) in 9 mL of a 1:1:1 mixture of CH3OH:THF:water is added LiOH (0.38 g, 9.0 mmol). The solution is stirred for 16 hours. After this time, the solution is concentrated to ⅓ its volume. The resulting solution is acidified to pH=3 with 1N HCl. The aqueous solution is extracted with CH2Cl2. The organic layer is dried over MgSO4, filtered and concentrated under vacuum. The title compound (0.32 g, 1.66 mmol) is obtained as a white solid. 1H NMR (CDCl3, 300 MHz) δ6.50 (d, 1H), 6.07 (d, 1H), 4.66 (s, 2H).

Workup

  1. concentrationAfter this time, the solution is concentrated
  2. extractionThe aqueous solution is extracted with CH2Cl2
  3. dry with materialThe organic layer is dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-032d8192a3e14c178693e45921beb9c9
Source dataset
uspto-grants-2009_11
Patent number
US07612075B2

Reaction notes

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