Ethyl 2-thiopheneglyoxylate → Ethyl 2-hydroxy-2-(thiophen-2-yl)acetate

HRID 1044050Notes

Reaction equation

HRID 1044050 reaction equation
[O:1]=[C:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[BH4-].[Na+]>C(O)C>[OH:1][CH:2]([C:8]1[S:9][CH:10]=[CH:11][CH:12]=1)[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 77693Ethyl 2-thiopheneglyoxylateHCID 4311764Sodium borohydride

Product 1

HCID 12266229Ethyl 2-hydroxy-2-(thiophen-2-yl)acetateYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of ethyl 2-oxo-2-(thiophen-2-yl)acetate (5.00 g, 27.1 mmol) in ethanol (50 ml) was cooled at 0° C. with an ice bath. NaBH4 (0.31 g, 8.14 mmol) was added in four portions under stirring. The mixture was stirred at 0° C. for 10 minutes, then allowed to warm at room temperature and stirred for additional 30 minutes. The reaction mixture was concentrated under vacuum and the residue was partitioned between Et2O and ice-cooled water. The organic layer was separated, washed with water and brine, dried over Na2SO4, filtered and evaporated (5.05 g, 91% yield).

Workup

  1. stirringThe mixture was stirred at 0° C. for 10 minutes
  2. stirringstirred for additional 30 minutes
  3. concentrationThe reaction mixture was concentrated under vacuum
  4. customthe residue was partitioned between Et2O and ice-
  5. temperaturecooled water
  6. customThe organic layer was separated
  7. washwashed with water and brine
  8. dry with materialdried over Na2SO4
  9. filtrationfiltered
  10. customevaporated (5.05 g, 91% yield)

Sources & evidence

ORD record
ord-3e39ef05f4384bee854de6d4a95b0226
Source dataset
uspto-grants-2013_10
Patent number
US08563577B2

Reaction notes

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