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

HRID 2211009Notes

Reaction equation

HRID 2211009 reaction equation
[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

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 807IodineHCID 8028Tetrahydrofuran2×HCID 229990Methyl 2-bromoacrylateHCID 10702996HCID 10702996, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 23994ZincCatalyst

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-9c09a4cb213f4fbfa03adc4d503255be
Source dataset
uspto-grants-1995_10
Patent number
US05461158

Reaction notes

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