[1-(2-Oxoethyl)cyclopropyl]acetonitrile → [1-(2-Hydroxypropyl)cyclopropyl]acetonitrile

HRID 1451530Notes

Reaction equation

HRID 1451530 reaction equation
[O:1]=[CH:2][CH2:3][C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1.[CH3:10][Mg]Cl>C1COCC1>[OH:1][CH:2]([CH3:10])[CH2:3][C:4]1([CH2:7][C:8]#[N:9])[CH2:6][CH2:5]1

Participants

4

Reactant 2

HCID 19041707[1-(2-Oxoethyl)cyclopropyl]acetonitrileHCID 178418332HCID 178418332, compound

Product 1

HCID 19041637[1-(2-Hydroxypropyl)cyclopropyl]acetonitrileYield 72.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a -5° C. solution of the aldehyde from Step 2 (3.00 g, 24.4 mmol) in 65 mL of THF was added methyl magnesium chloride (3.0M solution in THF, 9.5 mL, 29 mmol) and the reaction was stirred 2 h at 0° C. The reaction was quenched with 1M HCl and extracted with ethyl acetate. The organic extracts were washed with saturated NaHCO3 and brine and dried over MgSO4. Purification by flash chromatography (30% ethyl acetate/hexanes) provided 2.46 g of the title product.

Workup

  1. customThe reaction was quenched with 1M HCl
  2. extractionextracted with ethyl acetate
  3. washThe organic extracts were washed with saturated NaHCO3 and brine
  4. dry with materialdried over MgSO4
  5. customPurification by flash chromatography (30% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-5da4e2b5dce24acb903d596e2e70d048
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

Loading…