Diethyl Ether → 4-(cis-3-Allylcyclohexyloxymethyl)-2-(3-methylphenyl)-5-methyloxazole

HRID 858201

反応式

HRID 858201 の反応式
[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([OH:10])[CH2:5]1)[CH:2]=[CH2:3].[H-].[Na+].I[CH2:14][C:15]1[N:16]=[C:17]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)[O:18][C:19]=1[CH3:20].CCOCC>CN(C)C=O>[CH2:1]([C@@H:4]1[CH2:9][CH2:8][CH2:7][C@H:6]([O:10][CH2:14][C:15]2[N:16]=[C:17]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=3)[O:18][C:19]=2[CH3:20])[CH2:5]1)[CH:2]=[CH2:3]

参加物

6

反応物 4

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 219803084-Iodomethyl-5-methyl-2-m-tolyloxazoleHCID 58763359cis-3-Allylcyclohexanol

生成物 1

HCID 688571834-(cis-3-Allylcyclohexyloxymethyl)-2-(3-methylphenyl)-5-methyloxazole

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒2 回

実験手順

2 g of cis-3-allylcyclohexanol are dissolved in 30 ml of dimethylformamide, and 750 mg of sodium hydride (60% strength suspension in paraffin oil) are added. After 30 minutes, 6.7 g of 4-iodomethyl-5-methyl-2-(3-methylphenyl)oxazole, dissolved in 20 ml of dimethylformamide, are added dropwise. The mixture is stirred at room temperature for 1 hour. 200 ml of methy tert-buthyl ether are then added to the reaction mixture, and the mixture is washed three times with water. The organic phase is dried over magnesium sulfate and the solvent is then removed under reduced pressure. The residue is purified by RP-HPLC. This gives 1.56 g of 4-(cis-3-allylcyclohexyloxymethyl)-2-(3-methylphenyl)-5-methyloxazole as an oil. C21H27NO2 (325.45), MS (ESI): 326 (M+H+), Rf(n-heptane:ethylacetate=2:1)=0.28.

後処理

  1. additionare added dropwise
  2. washthe mixture is washed three times with water
  3. dry with materialThe organic phase is dried over magnesium sulfate
  4. customthe solvent is then removed under reduced pressure
  5. customThe residue is purified by RP-HPLC

出典と根拠

ORDレコード
ord-1ea7bf2aa6d04216be5e39b3b71bf910
出典データセット
uspto-grants-2006_12
特許番号
US07148246B2

関連ノート

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