(Trifluoromethyl)trimethylsilane → 6-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

HRID 2096780Notes

Reaction equation

HRID 2096780 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:26])[C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH2:20][C:19](=[O:22])[N:18]([CH2:23][CH3:24])[C:17]=2[CH:25]=1)=[O:12].[F:27][C:28]([Si](C)(C)C)([F:30])[F:29]>>[Cl:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[CH:4][C:3]=1[CH:10]([CH3:26])[C:11]([C:13]1[CH:14]=[CH:15][C:16]2[O:21][CH2:20][C:19](=[O:22])[N:18]([CH2:23][CH3:24])[C:17]=2[CH:25]=1)([OH:12])[C:28]([F:30])([F:29])[F:27]

Participants

3

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 666972276-[2-(2-Chloro-4-methoxy-phenyl)-propionyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 666972866-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one

Procedure

In analogy to Example 56, step 3, 6-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-4-ethyl-4H-benzo[1,4]oxazin-3-one (1.58 g) was reacted with (trifluoromethyl)-trimethylsilane. The product was purified by flash chromatography (silica gel, heptane/AcOEt 2:1) to give the title compound (1.58 g) as a white solid. MS (m/e)=444.3 [M+H+]

Workup

  1. customThe product was purified by flash chromatography (silica gel, heptane/AcOEt 2:1)

Sources & evidence

ORD record
ord-51065769ed214ca9b9c702a8a2ffb728
Source dataset
uspto-grants-2013_05
Patent number
US08450313B2

Reaction notes

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