Hydrochloric Acid → 4-(1-Benzylthio-1-methylethyl)-2-methylene-4-butanolide

HRID 2211009ノート

反応式

HRID 2211009 の反応式
[CH2:1]([S:8][C:9]([CH3:13])([CH3:12])[CH:10]=[O:11])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Cl.II.Br[C:18](=[CH2:23])[C:19]([O:21]C)=O.[CH2:24]1COCC1>[Zn]>[CH2:1]([S:8][C:9]([CH:10]1[O:11][C:19](=[O:21])[C:18](=[CH2:23])[CH2:24]1)([CH3:13])[CH3:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

7

反応物 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 8028Tetrahydrofuran2 回HCID 229990Methyl 2-bromoacrylateHCID 10702996HCID 10702996、化合物

生成物 1

HCID 152904644-(1-Benzylthio-1-methylethyl)-2-methylene-4-butanolide収率 97%

試薬・触媒・溶媒 1

HCID 23994Zinc触媒

実験手順

To a solution of 2-benzylthio-2-methylpropionaldehyde (3.26 g) in THF (80 ml), zinc dust (2.56 g) activated with hydrochloric acid and a small amount of iodine were added. To the mixture methyl 2-bromoacrylate (3.00 g) dissolved in THF (20 ml) was added dropwise. The mixture was stirred for 3 hours under ultrasonic irradiation and filtrated by celite. To the filtrate ether was added. The organic layer was washed with water and saturated sodium chloride solution, dried over anhydrous sodium sulfate and concentrated in vacuo. The oily residue was purified by silica gel column chromatography to give 4.31 g (97%) of the titled compound.

後処理

  1. additionwas added dropwise
  2. filtrationfiltrated by celite
  3. additionTo the filtrate ether was added
  4. washThe organic layer was washed with water and saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe oily residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-9c09a4cb213f4fbfa03adc4d503255be
出典データセット
uspto-grants-1995_10
特許番号
US05461158

反応ノート

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