Tetrahydrofuran → 4-(2,4-dimethoxyphenylcarbonyl)-2-ethyl-8-(prop-1-enyl)-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 76346

Reaction equation

HRID 76346 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[H-].[Na+].O1[CH:21]=[CH:20][CH2:19][C:18](=[O:22])[NH:17]1.[CH2:23]1[CH2:27][O:26][CH2:25][CH2:24]1>>[CH3:1][O:2][C:3]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:4]=1[C:5]([N:17]1[C:18](=[O:22])[CH:19]([CH2:20][CH3:21])[O:26][C:25]2[C:3]([CH:4]=[CH:8][CH3:9])=[CH:11][CH:27]=[CH:23][C:24]1=2)=[O:6]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 27347192,4-Dimethoxybenzoyl chlorideHCID 21873527Oxazinone

Product 1

HCID 680251834-(2,4-dimethoxyphenylcarbonyl)-2-ethyl-8-(prop-1-enyl)-2H-benzo[b][1,4]oxazin-3(4H)-oneYield 84%

Procedure

Procedure & NMR Data: 162 mg (2.5 eq, 0.8 mmol) of 2,4-Dimethoxybenzoyl chloride was added to a mixture of 49 mg (4 eq, 1.28 mmol) of NaH and 73 mg (0.32 mmol) of oxazinone P2 in THF (14 mL). 109 mg of P9 were obtained, yield 84%.

Workup

  1. custom109 mg of P9 were obtained

Sources & evidence

ORD record
ord-7e118ac479cc4682b6453e374ddeddfb
Source dataset
uspto-grants-2014_09
Patent number
US08835628B2

Linked notes

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