Dimethyl Sulfoxide → 2-[1-(2-Oxopropyl)cyclopropyl]acetonitrile

HRID 1451531Notes

Reaction equation

HRID 1451531 reaction equation
C(Cl)(=O)C(Cl)=O.CS(C)=O.[OH:11][CH:12]([CH3:20])[CH2:13][C:14]1([CH2:17][C:18]#[N:19])[CH2:16][CH2:15]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]=[C:12]([CH3:20])[CH2:13][C:14]1([CH2:17][C:18]#[N:19])[CH2:16][CH2:15]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 19041637[1-(2-Hydroxypropyl)cyclopropyl]acetonitrile

Product 1

HCID 190416812-[1-(2-Oxopropyl)cyclopropyl]acetonitrileYield 38.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a -78° C. solution of oxalyl chloride (0.70 mL, 8.0 mmol) in 40 mL of CH2Cl2 was added DMSO (0.62 mL, 8.7 mmol) and the resulting solution was stirred for 10 min. A solution of the alcohol from Step 3 (2.46 g, 17.7 mmol) in 5 mL CH2Cl2 was then added, and the mixture stirred 1 h at -78° C. Triethylamine (4.2 mL, 30 mmol) was then added, and the solution was allowed to warm to room temperature and stirred overnight. The reaction mixture was then partitioned between 1M HCl and CH2Cl2, and the organic layer was washed with saturated NaHCO3 and brine, dried over MgSO4 and evaporated. Purification of the residue by flash chromatography (25% ethyl acetate/hexanes) provided 927 mg of the title compound.

Workup

  1. stirringthe mixture stirred 1 h at -78° C
  2. stirringstirred overnight
  3. customThe reaction mixture was then partitioned between 1M HCl and CH2Cl2
  4. washthe organic layer was washed with saturated NaHCO3 and brine
  5. dry with materialdried over MgSO4
  6. customevaporated
  7. customPurification of the residue by flash chromatography (25% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-ce15eed8469d493eb8f5c3c784734347
Source dataset
uspto-grants-1997_02
Patent number
US05604253

Reaction notes

Loading…