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

HRID 2371497

Reaction equation

HRID 2371497 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 3283Diethyl EtherSolvent

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-2b2dee6f1c3241459509ee494d9a1377
Source dataset
uspto-grants-1992_03
Patent number
US05093356

Linked notes

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