Dimethyl Sulfoxide → HCID 22941134, compound

HRID 1602461Notes

Reaction equation

HRID 1602461 reaction equation
CS(C)=O.C(Cl)(=O)C(Cl)=O.[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C@@H:20]3[CH2:22][C@H:21]3[CH2:23][OH:24])[C:14]=2[CH2:13][CH2:12]1.C(N(CC)CC)C>C(Cl)Cl>[O:11]1[C:15]2[CH:16]=[CH:17][CH:18]=[C:19]([C@@H:20]3[CH2:22][C@H:21]3[CH:23]=[O:24])[C:14]=2[CH2:13][CH2:12]1

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 53689600HCID 53689600, compound

Product 1

HCID 22941134HCID 22941134, compoundYield 100.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

DMSO (1.6 g, 21 mmol) was added to oxalyl chloride in CH2Cl2 (7.4 mL of 2M solution, 14.8 mmole) at -78° C. The (-)-(trans)-2-(2,3-dihydrobenzofuran-4-yl)-cyclopropylmethanol (2.0 g, 10.5 mmol) in CH2Cl2 (15 mL) was added. The mixture was stirred for 20 min and then triethylamine (4.24 g, 42 mmol) was added. The mixture was warmed to room temperature and stirred for 30 min. The mixture was diluted with CH2Cl2 and washed with water, 1N HCl), and then 1N NaOH. The organic layer was dried and concentrated in vacuo to give the aldehyde product (1.98 g, 100%).

Workup

  1. stirringstirred for 30 min
  2. washwashed with water, 1N HCl), and then 1N NaOH
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-550f3607934940509ba461f5a335d6ab
Source dataset
uspto-grants-1999_11
Patent number
US05981571

Reaction notes

Loading…