Dimethyl Sulfide → HCID 77230662, compound

HRID 2173270Notes

Reaction equation

HRID 2173270 reaction equation
[CH:1]([CH:3]1[C:12]2[C:7](=[C:8]([C:13]#[N:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][O:5][CH2:4]1)=C.[O:15]=[O+][O-].S(C)C>C(Cl)Cl>[CH:1]([CH:3]1[C:12]2[C:7](=[C:8]([C:13]#[N:14])[CH:9]=[CH:10][CH:11]=2)[CH2:6][O:5][CH2:4]1)=[O:15]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 77230652HCID 77230652, compound

Product 1

HCID 77230662HCID 77230662, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 4-ethenyl-3,4-dihydro-1H-isochromene-8-carbonitrile (62 mg, 0.334 mmol) in DCM (10 mL) was bubbled with O3 for 10 mins at −78° C. until the blue color appeared. Then Me2S (1 mL) was added and the mixture was stirred at r.t. for 5 hours. Then the mixture was concentrated in vacuo to give the desired product 4-formyl-3,4-dihydro-1H-isochromene-8-carbonitrile, which can be used for next step without further purification.

Workup

  1. concentrationThen the mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-b8207e40ca6841e391086e473c569d9a
Source dataset
uspto-grants-2015_06
Patent number
US09056859B2

Reaction notes

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