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

HRID 660078Notes

Reaction equation

HRID 660078 reaction equation
[S:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6](=[O:12])[C:7]([O:9][CH2:10][CH3:11])=[O:8].[CH:13]1([Mg]Cl)[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1>C(OCC)C>[CH2:10]([O:9][C:7](=[O:8])[C:6]([CH:13]1[CH2:18][CH2:17][CH2:16][CH2:15][CH2:14]1)([OH:12])[C:2]1[S:1][CH:5]=[CH:4][CH:3]=1)[CH3:11]

Participants

4

Reactant 2

HCID 77693Ethyl 2-thiopheneglyoxylateHCID 178478990HCID 178478990, compound

Product 1

HCID 44147725Ethyl cyclohexyl(hydroxy)(thiophen-2-yl)acetate

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

To a stirred, cooled (0° C.) solution of ethyl thiophene-2-glyoxylate (125.6 g, 0.683 mol) in diethyl ether (2 litres) is added dropwise 2M cyclohexyl magnesium chloride in ether (400 ml, 0.8 mol) over 1 hour. After stirring at room temperature for 2 hours, the reaction is quenched by addition of saturated ammonium chloride solution (1 litre of a 270 g/l solution) and water (1 litre) ensuring the temperature does not rise above 20° C. The organic portion is separated and washed with brine (1 litre), dried over magnesium sulphate and concentrated in vacuo, to yield the titled compound as an orange oil which is used in the next step without further purification.

Workup

  1. customthe reaction is quenched by addition of saturated ammonium chloride solution (1 litre of a 270 g/l solution) and water (1 litre)
  2. customdoes not rise above 20° C
  3. customThe organic portion is separated
  4. washwashed with brine (1 litre)
  5. dry with materialdried over magnesium sulphate
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bf432eca4235415087e427a87215cdad
Source dataset
uspto-grants-2011_12
Patent number
US08084463B2

Reaction notes

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