Methanol → HCID 131727094, compound

HRID 2115602Notes

Reaction equation

HRID 2115602 reaction equation
[CH3:1][O:2][C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[CH:5]([C:8]([CH3:16])([CH3:15])[O:9][SiH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=C.N#N.CSC.C[OH:26]>ClCCl>[CH3:1][O:2][C:3](=[O:19])[C:4]([CH3:18])([CH3:17])[CH:5]([C:8]([CH3:16])([CH3:15])[O:9][SiH2:10][C:11]([CH3:14])([CH3:13])[CH3:12])[CH:6]=[O:26]

Participants

6

Reactant 4

HCID 887MethanolHCID 947NitrogenHCID 1068Dimethyl SulfideHCID 131727095HCID 131727095, compound

Product 1

HCID 131727094HCID 131727094, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of Example 2C (3.5 g, 12.2 mmol)in dichloromethane (25 mL) and methanol (2.5 mL) was cooled to −78° C. and O3 was bubbled for twenty-five minutes. The reaction was purged with N2 and DMS (5.29 g, 85.4 mmol) was added. The reaction was stirred at room temperature for three hours. The solvent was evaporated in vacuo and the product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50) to provide the title compound as an oil.

Workup

  1. customO3 was bubbled for twenty-five minutes
  2. additionwas added
  3. customThe solvent was evaporated in vacuo
  4. customthe product purified by flash column chromatography (hexanes:ethyl acetate) 100:0 to 50:50)

Sources & evidence

ORD record
ord-342d345cc0bb4a77abfef35614179033
Source dataset
uspto-grants-2008_10
Patent number
US07435833B2

Reaction notes

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