Hydrochloric Acid → Ethyl-4-(3-isopropyl-2-methoxyphenyl)-4-methyl-2-oxo-pentanoate

HRID 1443235ノート

反応式

HRID 1443235 の反応式
[Sn](Cl)(Cl)(Cl)Cl.[CH:6]([C:9]1[C:10]([O:19][CH3:20])=[C:11]([C:15](O)([CH3:17])[CH3:16])[CH:12]=[CH:13][CH:14]=1)([CH3:8])[CH3:7].[CH2:21]([O:23][C:24](=[O:32])[C:25]([O:27][Si](C)(C)C)=[CH2:26])[CH3:22].C(=O)([O-])[O-].[Na+].[Na+].Cl>ClCCl.O>[CH2:21]([O:23][C:24](=[O:32])[C:25](=[O:26])[CH2:27][C:15]([C:11]1[CH:12]=[CH:13][CH:14]=[C:9]([CH:6]([CH3:8])[CH3:7])[C:10]=1[O:19][CH3:20])([CH3:17])[CH3:16])[CH3:22]

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 10340Sodium Carbonate2 回HCID 24287Tin tetrachlorideHCID 111168062-Trimethylsilanyloxy-acrylic acid ethyl esterHCID 179891992-(3-Isopropyl-2-methoxyphenyl)propan-2-ol

生成物 1

HCID 17989132Ethyl-4-(3-isopropyl-2-methoxyphenyl)-4-methyl-2-oxo-pentanoate収率 49.3%

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒3 回

反応条件

温度
-72 °C

実験手順

15.3 ml (129.71 mmol) of tin tetrachloride is added in drops to a mixture, cooled to −72° C., that consists of 28.16 g (135.19 mmol) of 2-(3-isopropyl-2-methoxyphenyl)-propan-2-ol and 50.9 g (270.38 mmol) of 2-trimethylsilanyloxy-acrylic acid ethyl ester in 420 ml of dichloromethane. In this case, the temperature increased to −65° C. After 30 minutes of stirring in this temperature interval, the reaction mixture is poured onto a mixture that consists of saturated sodium carbonate solution and dichloromethane (in each case 250 ml). After 30 minutes of stirring at room temperature, the batch is transferred into a spherical separating funnel, and a 1:1 mixture that consists of water and dichloromethane is added until a phase separation takes place. After the organic phase is shaken with sodium carbonate, 1N HCl and water, it is dried with sodium sulfate. After the usual procedure, the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane). 20.44 g (48.35%) of the desired compound is obtained.

後処理

  1. temperatureIn this case, the temperature increased to −65° C
  2. additionthe reaction mixture is poured onto a mixture that
  3. stirringAfter 30 minutes of stirring at room temperature
  4. customthe batch is transferred into a spherical separating funnel
  5. additionis added until a phase separation
  6. dry with materialis dried with sodium sulfate
  7. customAfter the usual procedure, the residue is chromatographed on silica gel (mobile solvent: ethyl acetate/hexane)

出典と根拠

ORDレコード
ord-ef13a7846ab1487e8c46e74cbb13d7ca
出典データセット
uspto-grants-2010_02
特許番号
US07659297B2

反応ノート

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