Dimethyl Sulfide → HCID 59271849, compound

HRID 1893205Notes

Reaction equation

HRID 1893205 reaction equation
[O:1]=[O+][O-].[CH3:4][O:5][C@@H:6]([CH2:16][CH2:17][CH:18]=C)[CH2:7][O:8][CH2:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.CSC.C(N(CC)CC)C>ClCCl>[CH2:9]([O:8][CH2:7][C@@H:6]([O:5][CH3:4])[CH2:16][CH2:17][CH:18]=[O:1])[C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1

Participants

6

Reactant 4

HCID 1068Dimethyl SulfideHCID 8471TriethylamineHCID 24823OzoneHCID 68668293HCID 68668293, compound

Product 1

HCID 59271849HCID 59271849, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stream of ozone was dispersed into a cold (initial T=−78° C.) stirred solution of ({[(2S)-2-methoxyhex-5-en-1-yl]oxy}methyl)benzene (40 g, 182 mmol) in dichloromethane (1800 mL) until a blue color persisted. The solution was purged with nitrogen until a clear, colorless solution was obtained. Dimethyl sulfide (67.2 mL, 908 mmol) and triethylamine (76 mL, 545 mmol) were added. The stirred mixture was allowed to warm to room temperature over 60 minutes. (A test for peroxide with wet starch-iodide paper was negative.) The mixture was concentrated under reduced pressure to provide the crude title product which was used in the next step without purification.

Workup

  1. customThe solution was purged with nitrogen until a clear, colorless solution
  2. customwas obtained
  3. concentration) The mixture was concentrated under reduced pressure

Sources & evidence

ORD record
ord-2eee4b969c06416e9ca7d68dc04ce3f4
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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