Water → Ethyl 5-(hydroxymethyl)-2-thiophenecarboxylate

HRID 2202584Notes

Reaction equation

HRID 2202584 reaction equation
[S:1]1[C:5]([C:6](OCC)=[O:7])=[CH:4][CH:3]=[C:2]1[C:11]([O:13][CH2:14][CH3:15])=[O:12].[BH4-].[Na+].O>C(O)C>[OH:7][CH2:6][C:5]1[S:1][C:2]([C:11]([O:13][CH2:14][CH3:15])=[O:12])=[CH:3][CH:4]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4311764Sodium borohydrideHCID 149931952,5-Diethyl 2,5-thiophenedicarboxylate

Product 1

HCID 24729456Ethyl 5-(hydroxymethyl)-2-thiophenecarboxylateYield 52.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Diethyl 2,5-thiophenedicarboxylate (1.14 g, 5 mmol) synthesized in Production Example 71 was dissolved in ethanol, and sodium tetrahydroborate (113 mg, 3 mmol) was added thereto. The mixture was stirred for 3 days at a room temperature. After the completion of the reaction was confirmed by HPLC, water was added to the mixture, and the resulting mixture was concentrated under a reduced pressure. The residue was dissolved in ethyl acetate, washed with water and a saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate, and the solvent was distilled off. The resulting residue was purified by flash column chromatography (Yamazen Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=3:2) to give the title compound (491 mg, 52.7%) as an oily substance.

Workup

  1. additionwas added to the mixture
  2. concentrationthe resulting mixture was concentrated under a reduced pressure
  3. dissolutionThe residue was dissolved in ethyl acetate
  4. washwashed with water
  5. dry with materiala saturated sodium chloride aqueous solution, and then dried over anhydrous magnesium sulfate
  6. distillationthe solvent was distilled off
  7. customThe resulting residue was purified by flash column chromatography (Yamazen Hi-Flash column, silica gel, hexane/ethyl acetate (volume ratio)=3:2)

Sources & evidence

ORD record
ord-cc59a9ca134543fcb43ab990abb755f3
Source dataset
uspto-grants-2016_06
Patent number
US09365553B2

Reaction notes

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