Dimethyl Sulfide → HCID 87688530, compound

HRID 2173195Notes

Reaction equation

HRID 2173195 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[F:14])[CH:2]=C.[O:15]=[O+][O-].CSC>CO>[F: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 67516513HCID 67516513, compound

Product 1

HCID 87688530HCID 87688530, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 5-allyl-4-fluoro-2-benzofuran-1(3H)-one (30 mg, 0.16 mmol) in MeOH at −78° C. was bubbled ozone through until it turned light blue. After excess ozone was removed by bubbling nitrogen through the solution, dimethyl sulfide (0.1 mL, 1.1 mmol) was added into the reaction. The solution was allowed to warm to RT. The crude material was purified by MPLC to deliver (4-fluoro-1-oxo-1,3-dihydro-2-benzofuran-5-yl)acetaldehyde. LC-MS (IE, m/z): 195 [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-4a3847c9778d4c64a27ec1eb55896796
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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