Hydrochloric Acid → 5-(Tetrahydro-pyran-4-yl)-thiophene-3-carboxylic acid

HRID 1809049Notes

Reaction equation

HRID 1809049 reaction equation
[OH-].[K+].C([O:5][C:6]([C:8]1[CH:12]=[C:11]([CH:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[S:10][CH:9]=1)=[O:7])C.Cl>O>[O:16]1[CH2:15][CH2:14][CH:13]([C:11]2[S:10][CH:9]=[C:8]([C:6]([OH:7])=[O:5])[CH:12]=2)[CH2:18][CH2:17]1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 59542513ethyl 5-(tetrahydro-2H-pyran-4-yl)thiophene-3-carboxylate

Product 1

HCID 595425925-(Tetrahydro-pyran-4-yl)-thiophene-3-carboxylic acidYield 85.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

Potassium hydroxide (0.56 g, 10 mmol) in water (2 mL) was added to 5-(tetrahydro-pyran-4-yl)-thiophene-3-carboxylic acid ethyl ester (3.36 mmol) in IMS (6 mL). The reaction mixture was stirred for 1 hour then water was added and the mixture acidified to pH 7 with 1 N hydrochloric acid and then extracted with diethyl ether. The organic solution was dried over magnesium sulphate, filtered and the solvent evaporated to give the title compound (613 mg). LCMS m/z 211 [M−H]− RT=2.53 min (Analytical Method 4).

Workup

  1. extractionextracted with diethyl ether
  2. dry with materialThe organic solution was dried over magnesium sulphate
  3. filtrationfiltered
  4. customthe solvent evaporated

Sources & evidence

ORD record
ord-cf31ea8732fa476b91ec5df5799c3ab7
Source dataset
uspto-grants-2013_01
Patent number
US08362008B2

Reaction notes

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