Allyl bromide → Tert-butyl 4-(cis-3-allyloxycyclohexyl)-2-ethylbutyrate

HRID 347418ノート

反応式

HRID 347418 の反応式
[CH2:1]([CH:3]([CH2:11][CH2:12][C@H:13]1[CH2:18][CH2:17][CH2:16][C@@H:15]([OH:19])[CH2:14]1)[C:4]([O:6][C:7]([CH3:10])([CH3:9])[CH3:8])=[O:5])[CH3:2].[H-].[Na+].[CH2:22](Br)[CH:23]=[CH2:24].C(OC)(C)(C)C>CN(C)C=O>[CH2:24]([O:19][C@@H:15]1[CH2:16][CH2:17][CH2:18][C@H:13]([CH2:12][CH2:11][CH:3]([CH2:1][CH3:2])[C:4]([O:6][C:7]([CH3:10])([CH3:8])[CH3:9])=[O:5])[CH2:14]1)[CH:23]=[CH2:22]

参加物

6

反応物 4

HCID 7841Allyl bromide2 回HCID 15413tert-Butyl methyl etherHCID 24758Sodium hydride3 回HCID 69494197Tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)butyrate

生成物 1

HCID 69494301Tert-butyl 4-(cis-3-allyloxycyclohexyl)-2-ethylbutyrate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

1.19 g of tert-butyl 2-ethyl-4-(cis-3-hydroxycyclohexyl)butyrate are dissolved in 50 ml of dimethylformamide, and 210 mg g of sodium hydride (60% strength in paraffin oil) are added. The suspension is stirred at room temperature for 15 minutes, and 1.6 ml of allyl bromide are then added. After one hour, a further 320 mg of sodium hydride are added. After 12 hours of stirring at room temperature, another 320 mg of sodium hydride and then 1.6 ml of allyl bromide are metered in. Stirring at room temperature is continued for a further 12 hours. After addition of 200 ml of methyl tert-butyl ether, the mixture is washed three times with in each case 100 ml of water and the organic phase is separated off and dried over magnesium sulfate. The solvent is removed under reduced pressure. The residue is purified on silica gel using the mobile phase n-heptane:ethyl acetate=60:1=>30:1. This gives 770 mg of tert-butyl 4-(cis-3-allyloxycyclohexyl)-2-ethylbutyrate as an oil. C19H34O3 (310.48), Rf(n-heptane:ethyl acetate=5:1)=0.48.

後処理

  1. waitAfter one hour
  2. stirringAfter 12 hours of stirring at room temperature
  3. stirringStirring at room temperature
  4. waitis continued for a further 12 hours
  5. washthe mixture is washed three times with in each case 100 ml of water
  6. customthe organic phase is separated off
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent is removed under reduced pressure
  9. customThe residue is purified on silica gel using the mobile phase n-heptane

出典と根拠

ORDレコード
ord-281dd96c810a45158b2ea17bd3ab0c14
出典データセット
uspto-grants-2007_02
特許番号
US07173151B2

反応ノート

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