Stannane, hydroxytrimethyl- → 3-[(2,6-Dimethylphenoxy)methylthio]propanoic acid

HRID 1261381Notes

Reaction equation

HRID 1261381 reaction equation
[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:3]=1[O:4][CH2:5][S:6][CH2:7][CH2:8][C:9]([O:11]C)=[O:10].[OH-].C[Sn+](C)C>ClCCCl>[CH3:1][C:2]1[CH:16]=[CH:15][CH:14]=[C:13]([CH3:17])[C:3]=1[O:4][CH2:5][S:6][CH2:7][CH2:8][C:9]([OH:11])=[O:10]

Participants

4

Reactant 2

HCID 11217597Stannane, hydroxytrimethyl-HCID 68490521Methyl 3-[(2,6-dimethylphenoxy)methylthio]propanoate

Product 1

HCID 593974173-[(2,6-Dimethylphenoxy)methylthio]propanoic acidYield 83.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A 50-mL flask equipped with reflux condenser and a magnetic stirring bar was charged with 0.254 g (1 mmol) of methyl 3-[(2,6-dimethylphenoxy)methylthio]propanoate and 0.362 g (2 mmol) of trimethyltin hydroxide dissolved in 25 mL of 1,2-dichloroethane and was refluxed overnight under an argon atmosphere. The solvent was removed under reduced pressure, the organic residue was dissolved in 40 mL of ethyl acetate, extracted 3 times with 10 mL 5% HCl, then with 10 mL brine, and dried with anhydrous magnesium sulfate. The solvent was removed under reduced pressure, and the reddish residue was purified by normal-phase (COMBIFLASH) chromatography with a hexane/ethyl acetate (95:5, 7 minutes; 95:40, 15 minutes) to afford 0.2 g (83%) of 3-[(2,6-dimethylphenoxy)methylthio]propanoic acid 29. 1H NMR (400 MHz, CDCl3): 2.33 (s, 6H), 2.78-2.82 (t, 2H, J=7.2 Hz), 3.03-3.07 (t, 2H, J=7.2H), 4.99 (s, 2H), 6.94-7.04 (m, 3H), 10.98 (b, OH). MS (ESI): 241 [M+H]+; 263 [M+Na]+.

Workup

  1. customA 50-mL flask equipped
  2. temperaturewith reflux condenser and a magnetic stirring bar
  3. temperaturewas refluxed overnight under an argon atmosphere
  4. customThe solvent was removed under reduced pressure
  5. dissolutionthe organic residue was dissolved in 40 mL of ethyl acetate
  6. extractionextracted 3 times with 10 mL 5% HCl
  7. dry with materialwith 10 mL brine, and dried with anhydrous magnesium sulfate
  8. customThe solvent was removed under reduced pressure
  9. customthe reddish residue was purified by normal-phase (COMBIFLASH) chromatography with a hexane/ethyl acetate (95:5, 7 minutes; 95:40, 15 minutes)

Sources & evidence

ORD record
ord-31fc99d2151e4c3f9e1fcc45774cde96
Source dataset
uspto-grants-2013_06
Patent number
US08470861B2

Reaction notes

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