Dimethyl Sulfide → HCID 20781254, compound

HRID 2181275Notes

Reaction equation

HRID 2181275 reaction equation
[O:1]=[O+][O-].[F:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[C:12]1([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=C)=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:17][CH2:16][CH:15]([NH:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])[CH2:14][CH2:13]1.CSC>ClCCl.CO>[F:4][C:5]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:6]=1[C:12]1([S:26]([C:29]2[CH:34]=[CH:33][C:32]([CH:35]=[O:1])=[CH:31][CH:30]=2)(=[O:28])=[O:27])[CH2:17][CH2:16][CH:15]([NH:18][S:19]([C:22]([F:25])([F:24])[F:23])(=[O:21])=[O:20])[CH2:14][CH2:13]1

Participants

5

Reactant 3

HCID 1068Dimethyl SulfideHCID 24823OzoneHCID 20781256HCID 20781256, compound

Product 1

HCID 20781254HCID 20781254, compound

Reagents, catalysts & solvents 1

HCID 21226129Dichloromethane methanolSolvent

Procedure

Ozone was bubbled through a solution of the product of Example 79 (2.5 g, 4.9 mmol) in dichloromethane/methanol (125 ml/25 ml) at −78° C. until a blue colour was observed. Oxygen was bubbled through the mixture for 10 minutes until the blue colour disappeared. The mixture was quenched with dimethyl sulfide (2.16 ml, 29.5 mmol), allowed to warm to room temperature and stirred for 16 hours. The mixture was concentrated in vacuo to give an oil (2.80 g), which was chromatographed on silica, eluting with 20% ethyl acetate/isohexane to give the aldehyde (2.18 g, 87%). 1H NMR (CDCl3, 360 MHz): 1.59-1.70 (2H, m), 2.04-2.09 (2H, m), 2.48 (2H, t, J=12.3), 2.61-2.68 (2H, m), 3.82 (1H, m), 5.75 (1H, d, J=7.7), 6.77-6.86 (1H, m), 7.07-7.11 (2H, m), 7.57 (2H, d, J=8.1), 7.90 (2H, d, J=8.3), 10.10 (1H, s)

Workup

  1. customOxygen was bubbled through the mixture for 10 minutes until the blue colour
  2. concentrationThe mixture was concentrated in vacuo

Sources & evidence

ORD record
ord-3de8ddeb5aed44f294a54b00c0913426
Source dataset
uspto-grants-2005_05
Patent number
US06890956B2

Reaction notes

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