Dimethyl Sulfoxide → HCID 22153776, compound

HRID 1111189Notes

Reaction equation

HRID 1111189 reaction equation
CS(C)=O.[C:5]([O:8][C:9]1[C:10]([CH3:23])=[C:11]([CH3:22])[C:12]2[O:16][C:15]([CH2:18]Br)([CH3:17])[CH2:14][C:13]=2[C:20]=1[CH3:21])(=[O:7])[CH3:6].[C-:24]#[N:25].[Na+]>O>[C:5]([O:8][C:9]1[CH:10]=[CH:11][C:12]2[O:16][CH2:15][CH2:14][C:13]=2[CH:20]=1)(=[O:7])[CH3:6].[C:5]([O:8][C:9]1[C:10]([CH3:23])=[C:11]([CH3:22])[C:12]2[O:16][C:15]([CH2:18][C:24]#[N:25])([CH3:17])[CH2:14][C:13]=2[C:20]=1[CH3:21])(=[O:7])[CH3:6]

Participants

6

Reactant 3

HCID 679Dimethyl SulfoxideHCID 8929Sodium CyanideHCID 15086718HCID 15086718, compound

Product 2

HCID 22153776HCID 22153776, compoundHCID 22153778HCID 22153778, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

To a dimethyl sulfoxide (5 ml) solution of 5-acetoxy-2-bromomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran [1.5 g(4.58 mmol)] was added sodium cyanide [270 mg (5.5 mmol)], and the mixture was stirred at 80° C. for 6 hours under argon atmosphere. The reaction mixture was, after cooling, diluted with water, and subjected to extraction with ethyl acetate. The extract was washed with water and dried, followed by distilling off the solvent. The residue was purified by means of a silica gel column chromatography [hexane - isopropyl ether (2:1)] to obtain 5-acetoxy-2,3-dihydrobenzofuran (Compound 6) (350 mg) and 5-acetoxy-2-cyanomethyl-2,4,6,7-tetramethyl-2,3-dihydrobenzofuran (Compound 5)(158 mg).

Workup

  1. temperatureafter cooling
  2. extractionsubjected to extraction with ethyl acetate
  3. washThe extract was washed with water
  4. customdried
  5. distillationby distilling off the solvent
  6. customThe residue was purified by means of a silica gel column chromatography [hexane - isopropyl ether (2:1)]

Sources & evidence

ORD record
ord-9cfd65791fe04a64a039d6a46ca40354
Source dataset
uspto-grants-1990_12
Patent number
US04978761

Reaction notes

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