Hydrochloric Acid → HCID 14989019, compound

HRID 2248279Notes

Reaction equation

HRID 2248279 reaction equation
[CH3:1][O:2][C:3](=[O:13])[C:4]([CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=[CH2:5].C[O-].[Na+].[CH3:17][CH:18]([SH:20])[CH3:19].Cl>CO.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:13])[CH:4]([CH2:6][C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)[CH2:5][S:20][CH:18]([CH3:19])[CH3:17]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 63642-PropanethiolHCID 575761Methyl 2-benzylprop-2-enoateHCID 10942334Sodium Methoxide

Product 1

HCID 14989019HCID 14989019, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of methyl-2-benzylacrylate (20 gm. 0.113 mol) in methanol (100 ml) at room temperature was added a solution of sodium methoxide (2N, 17 ml) followed by isopropylthiol (12.56 ml). TLC (4:1, Hexanes: ethyl acetate) showed reaction to be complete after 30 min. The reaction mixture was made acidic with 1N HCl and extracted three times with ethyl acetate. The combined organic fractions were dried over NaSO4, filtered and evaporated in vacuo. The crude product was purified by chromatography (silica 4:1, hexanes: ethyl acetate to give methyl-3-isopropylthio-2-benzylpropionate.

Workup

  1. customreaction
  2. extractionextracted three times with ethyl acetate
  3. dry with materialThe combined organic fractions were dried over NaSO4
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by chromatography (silica 4:1, hexanes

Sources & evidence

ORD record
ord-807d00fbba0e45f5b3f53d579bdbade2
Source dataset
uspto-grants-1991_08
Patent number
US05039664

Reaction notes

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