Dimethyl Sulfoxide → 1-(2-Oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

HRID 2056755Notes

Reaction equation

HRID 2056755 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[OH:11][CH2:12][CH2:13][CH:14]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:18]=2[CH2:17][CH2:16][O:15]1.C(N(CC)CC)C>ClCCl>[O:11]=[CH:12][CH2:13][CH:14]1[C:19]2[CH:20]=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:18]=2[CH2:17][CH2:16][O:15]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 236356931-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Product 1

HCID 865960151-(2-Oxoethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Dimethylsulfoxide (0.35 mL, 5 mmol) and oxalyl chloride (2M in dichloromethane) (2.2 mL, 4.4 mmol) were stirred in dichloromethane (30 mL) under nitrogen at −78° C. After 10 min, 1-(2-hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-carbonitrile (0.48 g, 2.4 mmol) in dichloromethane (50 mL) was added dropwise and the solution stirred at −78° C. for 1 h, before triethylamine (2.5 mL, 18 mmol) was added slowly. The reaction was allowed to warm to room temperature and after 2 h the reaction was quenched by addition of water. Removal of the solvent in vacuo yielded the title compound, which was used in the next step without further purification.

Workup

  1. additionwas added slowly
  2. customwas quenched by addition of water
  3. customRemoval of the solvent in vacuo

Sources & evidence

ORD record
ord-453821344482470bb6ee854bdebd2b82
Source dataset
uspto-grants-2008_02
Patent number
US07335660B2

Reaction notes

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