Hydrochloric Acid → Methyl 5-(hydroxymethyl)thiophene-3-carboxylate

HRID 450756

Reaction equation

HRID 450756 reaction equation
[CH:1]([C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1)=[O:2].C1COCC1.[BH4-].[Na+].Cl>CO>[OH:2][CH2:1][C:3]1[S:7][CH:6]=[C:5]([C:8]([O:10][CH3:11])=[O:9])[CH:4]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 818925Methyl 5-formylthiophene-3-carboxylateHCID 4311764Sodium borohydride

Product 1

HCID 12926498Methyl 5-(hydroxymethyl)thiophene-3-carboxylateYield 96.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a mixed liquid of 5.00 g of methyl 5-formylthiophene-3-carboxylate and 50 ml of THF was added 0.67 g of sodium borohydride under ice-cooling. To the reaction solution was added dropwise 5 ml of methanol, followed by stirring for 1 hour under ice-cooling. The reaction solution was added with 1 M hydrochloric acid, extracted with ethyl acetate, and washed with a saturated aqueous sodium hydrogen carbonate solution and a saturated aqueous sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and the solvent was then evaporated to obtain 4.86 g of methyl 5-(hydroxymethyl)thiophene-3-carboxylate as a pale yellow oily substance.

Workup

  1. temperaturecooling
  2. temperaturecooling
  3. extractionextracted with ethyl acetate
  4. washwashed with a saturated aqueous sodium hydrogen carbonate solution
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customthe solvent was then evaporated

Sources & evidence

ORD record
ord-e0ebe0a08b1340dbb9a91b79ccbe51bc
Source dataset
uspto-grants-2013_07
Patent number
US08486970B2

Linked notes

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