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

HRID 2211009노트

반응식

HRID 2211009 반응식
[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

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 8028Tetrahydrofuran2회HCID 229990Methyl 2-bromoacrylateHCID 10702996HCID 10702996, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 23994Zinc촉매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-9c09a4cb213f4fbfa03adc4d503255be
출처 데이터셋
uspto-grants-1995_10
특허 번호
US05461158

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