Hydrochloric Acid → Methyl 2-methyl-3-(4-methylthiobenzyl)inden-1-ylacetate

HRID 379641Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 379641
[CH3:1][CH:2]1[CH:10]([CH2:11][C:12]2[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=2)[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[C:3]1=O.Br[CH2:22][C:23]([O:25][CH3:26])=[O:24].II.Cl>CCOCC.[Zn]>[CH3:1][C:2]1[CH:3]([CH2:22][C:23]([O:25][CH3:26])=[O:24])[C:4]2[C:9]([C:10]=1[CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)=[CH:8][CH:7]=[CH:6][CH:5]=2

Komponenten

7

Edukt 4

HCID 313Hydrochloric AcidHCID 807IodineHCID 60984Methyl bromoacetateHCID 183674562-Methyl-3-(4-methylthiobenzyl)-1-indanone

Produkt 1

HCID 18367447Methyl 2-methyl-3-(4-methylthiobenzyl)inden-1-ylacetate

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23994ZincKatalysatorHCID 3283Diethyl EtherLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of the indanone derivative from Step 1 (885 mg, 3.14 mmol) in ether (20 mL) were added successively zinc (840 mg, 12.8 mmol), methyl bromoacetate (0.5 mL, 5 mmol) and iodine (200 mg). The reaction mixture was refluxed for 3 hours, then cooled to 0° C. and 6N aqueous HCl was added dropwise until the zinc complex was completely decomposed. The organic layer was decanted, washed with brine, dried over Na2SO4 and evaporated to dryness. The oily residue was dissolved in formic acid and evaporated to dryness to complete the dehydration of the intermediate methyl [1-hydroxy-2-methyl-3-(4-methylthiobenzyl)indan-1-yl]acetate. The resulting oily residue was chromatographed on silica gel eluting with a 1:19 mixture of ethyl acetate-hexane to afford pure title compound as an oil.

Aufarbeitung

  1. temperatureThe reaction mixture was refluxed for 3 hours
  2. customThe organic layer was decanted
  3. washwashed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to dryness
  6. dissolutionThe oily residue was dissolved in formic acid
  7. customevaporated to dryness
  8. customThe resulting oily residue was chromatographed on silica gel eluting with a 1:19 mixture of ethyl acetate-hexane

Quellen und Nachweise

ORD-Eintrag
ord-3b1aab1c433143d5836a91946510fbde
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06300346B1

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