Ethyl 2-formylcyclopropanecarboxylate → HCID 90736744, compound

HRID 657690Notes

Reaction equation

HRID 657690 reaction equation
[CH:1]([CH:3]1[CH2:5][CH:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:2].[C:11]([Mg]Br)#[CH:12]>O1CCCC1>[OH:2][CH:1]([C@@H:3]1[CH2:5][C@H:4]1[C:6]([O:8][CH2:9][CH3:10])=[O:7])[C:11]#[CH:12]

Participants

4

Reactant 2

HCID 89334Ethyl 2-formylcyclopropanecarboxylateHCID 178418486HCID 178418486, compound

Product 1

HCID 90736744HCID 90736744, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of ethyl 2-formyl-1-cyclopropanecarboxylate (predominately trans, 331 μL, 2.5 mmol) in tetrahydrofuran (5 mL) was cooled down to −70° C. Ethynylmagnesium bromide (0.5 M in tetrahydrofuran, 5 mL, 2.5 mmol) was added to the above solution under an atmosphere of nitrogen dropwise, and stirred at −70° C. for 1 h. The reaction was quenched with water, and extracted with ethyl acetate. The organic phase was washed with brine, dried over MgSO4, filtered and concentrated to get 419 mg of the title compound (yield 100%, unpurified) as a pale yellow oil.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. washThe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-1eac66e3e046476ba4698fe7abba3d05
Source dataset
uspto-grants-2011_12
Patent number
US08076344B2

Reaction notes

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