Dimethyl Sulfide → HCID 77230670, compound

HRID 2173192Notes

Reaction equation

HRID 2173192 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[Cl:14])[CH:2]=C.[O:15]=[O+][O-].CSC>CO>[Cl:14][C:5]1[C:6]2[CH2:10][O:9][C:8](=[O:11])[C:7]=2[CH:12]=[CH:13][C:4]=1[CH2:1][CH:2]=[O:15]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 67516453HCID 67516453, compound

Product 1

HCID 77230670HCID 77230670, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-allyl-4-chloro-2-benzofuran-1(3H)-one (80 mg, 0.38 mmol) in MeOH at −78° C. was bubbled ozone through until it turned light blue. After xcess 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 deliver (4-chloro-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde. LC-MS (IE, m/z): 211 [M+1]+.

Workup

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

Sources & evidence

ORD record
ord-10e5ad3926374392839e10c5f7ad6574
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

Loading…