1,2-Dibromoethane → 2-[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole

HRID 38316

反応式

HRID 38316 の反応式
[Mg].BrCCBr.Br[CH:7]([CH3:15])[CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O1CCN=C1.[CH3:21][C:22]1([CH3:39])[CH2:26][O:25][C:24]([C:27]2[CH:32]=[C:31]([O:33][CH3:34])[C:30]([O:35][CH3:36])=[CH:29][C:28]=2OC)=[N:23]1>O1CCCC1.CCCCCC.C(OCC)(=O)C>[CH3:36][O:35][C:30]1[C:31]([O:33][CH3:34])=[CH:32][C:27]([C:24]2[O:25][CH2:26][C:22]([CH3:21])([CH3:39])[N:23]=2)=[C:28]([CH:7]([CH3:15])[CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH:29]=1

参加物

7

反応物 4

HCID 78391,2-DibromoethaneHCID 102754(2-Bromopropyl)benzeneHCID 5462224MagnesiumHCID 670534204,4-Dimethyl-2-(2,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazole oxazoline

生成物 1

HCID 595987102-[4,5-Dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole収率 60.9%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒2 回HCID 21226206Ethyl acetate hexane溶媒

反応条件

温度
40 °C

実験手順

To a rapidly stirring suspension of magnesium turnings (1.32 g, 54.5 mol) and in 35 mL tetrahydrofuran (THF) was added 1,2-dibromoethane (0.10 mL) in one portion. 2-bromo-1-phenylpropane (10.86 g, 54.5 mmol) was added at a rate that maintained the internal temperature at 40° C. After 2.5 hours the cloudy suspension was transferred via canula to a solution of 4,4-dimethyl-2-(2,4,5-trimethoxy-phenyl)-4,5-dihydro-oxazole oxazoline (10.013 g, 36.4 mmol) in 50 mL THF. After 18 hours the solution cooled to 0° C. and quenched by the slow addition of 10% NH4Cl. 500 mL H2O was added and the mixture was extracted with ethyl acetate, washed with H2O, and washed with brine. The combined organics were dried over Na2SO4, filtered and concentrated in vacuo to give a crude solid. Purifications via flash chromatography (4:1 hexane/ethyl acetate) afforded 2-[4,5-dimethoxy-2-(1-methyl-2-phenyl-ethyl)-phenyl]-4,4-dimethyl-4,5-dihydro-oxazole as a clear viscous oil (7.833 g, 41%).

後処理

  1. temperatureAfter 18 hours the solution cooled to 0° C.
  2. customquenched by the slow addition of 10% NH4Cl
  3. addition500 mL H2O was added
  4. extractionthe mixture was extracted with ethyl acetate
  5. washwashed with H2O
  6. washwashed with brine
  7. dry with materialThe combined organics were dried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customto give a crude solid

出典と根拠

ORDレコード
ord-3d65a80ba6e24d0c92b143d4223fa8e5
出典データセット
uspto-grants-2013_09
特許番号
US08524725B2

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