Hydrochloric Acid → Tert-butyl 2-methylthio-6-n-hexylcinnamate

HRID 1086369

反応式

HRID 1086369 の反応式
C(NC(C)C)(C)C.C([Li])CCC.C[Si]([CH2:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19])(C)C.[CH3:25][S:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:28]=1[CH:29]=O.Cl>C1COCC1>[CH3:25][S:26][C:27]1[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH3:40])[C:28]=1[CH:29]=[CH:17][C:18]([O:20][C:21]([CH3:24])([CH3:23])[CH3:22])=[O:19]

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 7912DiisopropylamineHCID 995271,1-Dimethylethyl trimethylsilylacetateHCID 150081552-Methylthio-6-n-hexylbenzaldehydeHCID 178418339Butyllithium

生成物 1

HCID 54465638Tert-butyl 2-methylthio-6-n-hexylcinnamate

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

To a solution of lithium diisopropylamide, afforded by combining 3.4 g of diisopropylamine with 26 ml of n-butyllithium, at -40° C. in THF is added tert-butyl trimethylsilylacetate (8 g, 0.042 mmol) and the mixture stirred for 1 hour. To the reaction mixture is added 2-methylthio-6-n-hexylbenzaldehyde (7.08 g, 0.03 mmol) dropwise and stirred for 2 hours at -40° C. The reaction mixture is allowed to warm to -10° C. and cold lN HCl poured in. The mixture is extracted with diethyl ether. The extracts are washed with water and then brine, dried over MgSO4 and concentrated to afford tert-butyl 2-methylthio-6-n-hexylcinnamate which is hydrolyzed in methylene chloride with trifluoroacetic acid by refluxing overnight to afford the subtitle compound.

後処理

  1. stirringstirred for 2 hours at -40° C
  2. extractionThe mixture is extracted with diethyl ether
  3. washThe extracts are washed with water
  4. dry with materialbrine, dried over MgSO4
  5. concentrationconcentrated

出典と根拠

ORDレコード
ord-819f0ae255ac49a6a097e30ab4ddc585
出典データセット
uspto-grants-1991_07
特許番号
US05028629

関連ノート

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