Hydrochloric Acid → 4-(1-Benzylthio-1-methylethyl)-3-methyl-2-methylene-4-butanolide

HRID 2211011ノート

反応式

HRID 2211011 の反応式
Cl.[CH2:2]([S:9][C:10]([CH3:14])([CH3:13])[CH:11]=[O:12])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.Br[CH2:16]/[C:17](=[CH:22]\[CH3:23])/[C:18](OC)=[O:19].[Cl-].[NH4+]>C1COCC1.[Zn]>[CH2:2]([S:9][C:10]([CH:11]1[O:12][C:18](=[O:19])[C:17](=[CH2:16])[CH:22]1[CH3:23])([CH3:14])[CH3:13])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 10702996HCID 10702996、化合物HCID 11019705Methyl 2-bromomethylcrotonate

生成物 1

HCID 193781174-(1-Benzylthio-1-methylethyl)-3-methyl-2-methylene-4-butanolide

試薬・触媒・溶媒 2

HCID 23994Zinc触媒HCID 8028Tetrahydrofuran溶媒3 回

実験手順

To a stirred suspension of zinc dust (0.77 g) activated with hydrochloric acid in THF (20 ml), 2-benzylthio-2-methylpropionaldehyde (2.00 g) dissolved in THF (10 ml) and methyl 2-bromomethylcrotonate (2.19 g) dissolved in THF (10 ml) were added dropwise in the order named at about 30° C. under nitrogen atmosphere and ultrasonic irradiation. The mixture was stirred over night at room temperature. Saturated aqueous ammonium chloride solution was added to the mixture and the mixture was filtered by celite. A reaction product was extracted with ethyl acetate from the filtrate. The organic layer was washed with 1N hydrochloric acid, water and then saturated sodium chloride solution. The organic layer was dried over anhydrous magnesium sulfate and concentrated in vacuo. The oily residue was purified and separated by silica gel column chromatography to give the each titled compound.

後処理

  1. additionwere added dropwise in the order
  2. customnamed at about 30° C. under nitrogen atmosphere
  3. customultrasonic irradiation
  4. filtrationthe mixture was filtered by celite
  5. extractionA reaction product was extracted with ethyl acetate from the filtrate
  6. washThe organic layer was washed with 1N hydrochloric acid, water
  7. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe oily residue was purified
  10. customseparated by silica gel column chromatography

出典と根拠

ORDレコード
ord-4682e261ff064b0f97ba73ccc854632d
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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