Dimethyl Sulfoxide → HCID 15086717, compound

HRID 1111188Notes

Reaction equation

HRID 1111188 reaction equation
C(Cl)Cl.C(Cl)(=O)C(Cl)=O.CS(C)=O.[C:14]([O:17][C:18]1[C:19]([CH3:32])=[C:20]([CH3:31])[C:21]2[O:25][C:24]([CH2:27][OH:28])([CH3:26])[CH2:23][C:22]=2[C:29]=1[CH3:30])(=[O:16])[CH3:15]>C(N(CC)CC)C>[C:14]([O:17][C:18]1[C:19]([CH3:32])=[C:20]([CH3:31])[C:21]2[O:25][C:24]([CH:27]=[O:28])([CH3:26])[CH2:23][C:22]=2[C:29]=1[CH3:30])(=[O:16])[CH3:15]

Participants

6

Reactant 4

HCID 679Dimethyl SulfoxideHCID 6344Dichloromethane2×HCID 65578Oxalyl chlorideHCID 15086716HCID 15086716, compound

Product 1

HCID 15086717HCID 15086717, compoundYield 96.7%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

To a methylene chloride solution (50 ml) of oxalyl chloride (2 ml) was added dropwise at -60° C. dimethylsulfoxide (4 ml). The mixture was stirred for 10 minutes, and there was then added dropwise a methylene chloride solution (10 ml) of 5-acetoxy-2-hydroxymethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran [5.0 g (19 mmol)]. The reaction mixture was stirred for 15 minutes, and there was added triethylamine (15 ml), and the mixture was stirred for further 10 minutes. The reaction mixture was washed with water and dried, followed by distilling off the solvent. The residue was crystallized from isopropylether-hexane to obtain 5-acetoxy-2-formyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (yield 96.7%), m.p. 78°-79° C.

Workup

  1. stirringThe reaction mixture was stirred for 15 minutes
  2. stirringthe mixture was stirred for further 10 minutes
  3. washThe reaction mixture was washed with water
  4. customdried
  5. distillationby distilling off the solvent
  6. customThe residue was crystallized from isopropylether-hexane

Sources & evidence

ORD record
ord-27b6245f1e5b4643b510c0affab726ab
Source dataset
uspto-grants-1990_12
Patent number
US04978761

Reaction notes

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