Dimethyl Sulfoxide → HCID 22941134, compound

HRID 342101Notes

Reaction equation

HRID 342101 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
  3. customThe organic layer was dried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1de4004fb97846159e8630775593daa2
Source dataset
uspto-grants-1999_01
Patent number
US05856529

Reaction notes

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