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

HRID 2386778Notes

Reaction equation

HRID 2386778 reaction equation
[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:14](=[O:26])[CH:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[Cl:25])[CH3:16])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:27])[CH:2]=[CH2:3].[F:28][C:29]([Si](C)(C)C)([F:31])[F:30]>>[CH2:1]([N:4]1[C:9]2[CH:10]=[C:11]([C:14]([OH:26])([C:29]([F:31])([F:30])[F:28])[CH:15]([C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][C:18]=3[Cl:25])[CH3:16])[CH:12]=[CH:13][C:8]=2[O:7][CH2:6][C:5]1=[O:27])[CH:2]=[CH2:3]

Participants

3

Reactant 2

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 666972384-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 675466024-Allyl-6-[2-(2-chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-4H-benzo[1,4]oxazin-3-one

Procedure

In analogy to Example 56, step 3, 4-allyl-6-[2-(2-chloro-4-methoxy-phenyl)-propionyl]-4H-benzo[1,4]oxazin-3-one (7.2 g) was reacted with (trifluoromethyl)-trimethylsilane. The product was purified by crystallization with heptane/AcOEt (4:1) to give the title compound (4.45 g) as an off-white solid. MS (m/e)=456.3 [M+H+].

Workup

  1. customThe product was purified by crystallization with heptane/AcOEt (4:1)

Sources & evidence

ORD record
ord-cbd79835a4a14a328d9e5eb638deb4f5
Source dataset
uspto-grants-2012_09
Patent number
US08268820B2

Reaction notes

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