Dimethyl Sulfide → HCID 178520681, compound

HRID 2078369Notes

Reaction equation

HRID 2078369 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7]([OH:17])=[C:6]([C:18](=[O:23])[CH2:19][CH2:20][CH:21]=C)[C:5]2=[O:24].[O:25]=[O+][O-].CSC>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[C:8]1([CH2:13][CH2:12][O:11][CH2:10][CH2:9]1)[C:7]([OH:17])=[C:6]([C:18](=[O:23])[CH2:19][CH2:20][CH:21]=[O:25])[C:5]2=[O:24]

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 178446978HCID 178446978, compound

Product 1

HCID 178520681HCID 178520681, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

A mixture of 6-chloro-2-hydroxy-3-(4-pentenoyl)-2′,3′,5′,6′-tetrahydro-4H-spiro[naphthalene-1,4′-pyran]-4-one (0.65 g, 1.9 mmol) in 50 mL DCM was stirred at −78° C. and treated with O3 until the solution remained blue. The mixture was stirred at −78° C. for 30 minutes and then treated with 1 mL dimethyl sulfide and stirred from −78° C. to 0° C. for 2 hours. The mixture was concentrated in vacuo and purified by column eluting with 40:100=EtOAc/hexane to give the desired product. MS m/e: 349 (M+H)+.

Workup

  1. stirringThe mixture was stirred at −78° C. for 30 minutes
  2. stirringstirred from −78° C. to 0° C. for 2 hours
  3. concentrationThe mixture was concentrated in vacuo
  4. custompurified by column
  5. washeluting with 40:100=EtOAc/hexane

Sources & evidence

ORD record
ord-a9941a1514d1406583a8d598e55580a4
Source dataset
uspto-grants-2011_04
Patent number
US07928139B2

Reaction notes

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