Dimethyl Sulfide → HCID 77230670, compound

HRID 1465779Notes

Reaction equation

HRID 1465779 reaction equation
[O:1]=[O+][O-].[CH2:4]([C:7]1[CH:16]=[CH:15][C:10]2[C:11](=[O:14])[O:12][CH2:13][C:9]=2[C:8]=1[Cl:17])[CH:5]=C.CSC>CO>[Cl:17][C:8]1[C:9]2[CH2:13][O:12][C:11](=[O:14])[C:10]=2[CH:15]=[CH:16][C:7]=1[CH2:4][CH:5]=[O:1]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67516453HCID 67516453, compound

Product 1

HCID 77230670HCID 77230670, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Ozone was bubbled through a solution of 5-allyl-4-chloro-2-benzofuran-1(3H)-one (80 mg, 0.38 mmol) in MeOH at −78° C. until it turned light blue. After excess ozone was removed by bubbling nitrogen through the solution, dimethyl sulfide (0.57 mL, 7.7 mmol) was added into the reaction. The solution was allowed to warm to RT. The crude material was purified by MPLC to provide (4-chloro-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde. LC-MS (IE, m/z): 211 [M+1]+.

Workup

  1. customAfter excess ozone was removed
  2. additionwas added into the reaction
  3. customThe crude material was purified by MPLC

Sources & evidence

ORD record
ord-9136134471be4710ae6193ec963ba6b2
Source dataset
uspto-grants-2015_04
Patent number
US08999991B2

Reaction notes

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