Dimethyl Sulfide → HCID 77230672, compound

HRID 2173184Notes

Reaction equation

HRID 2173184 reaction equation
[CH2:1]([C:4]1[CH:13]=[CH:12][C:7]2[C:8](=[O:11])[O:9][CH2:10][C:6]=2[C:5]=1[CH2:14][CH2:15][CH3:16])[CH:2]=C.[O:17]=[O+][O-].CSC>CO>[O:11]=[C:8]1[C:7]2[CH:12]=[CH:13][C:4]([CH2:1][CH:2]=[O:17])=[C:5]([CH2:14][CH2:15][CH3:16])[C:6]=2[CH2:10][O:9]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67516171HCID 67516171, compound

Product 1

HCID 77230672HCID 77230672, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To the flask charged with 5-allyl-4-propyl-2-benzofuran-1(3H)-one (60 mg) was added methanol (10 mL). The solution was chilled to −78° C. before ozone was bubbled through. Ozone was stopped when the solution turned light blue. Excess ozone was removed by bubbling nitrogen through the solution, which was followed by addition of dimethyl sulfide (170 mg, 2.8 mmol). The mixture was allowed to warm to RT. The desired product, (1-oxo-4-propyl-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde, was purified by silica gel chromatography.

Workup

  1. customwas bubbled through
  2. customExcess ozone was removed
  3. customby bubbling nitrogen through the solution, which
  4. customThe desired product, (1-oxo-4-propyl-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde, was purified by silica gel chromatography

Sources & evidence

ORD record
ord-a9b40d913c284fa8bfafbaaf449f58be
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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