Acetic Acid → HCID 67851956, compound

HRID 486812Notes

Reaction equation

HRID 486812 reaction equation
[SH:1][CH2:2][CH2:3][C:4]([OH:6])=O.[CH3:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1C(=O)C=C[C:13]2=[O:18].[C:20]([O:23]CC)(=[O:22])[CH3:21].[C:26](O)(=O)C>O.C(O)C>[CH3:7][C:8]1[CH:17]=[CH:16][CH:15]=[C:14]2[C:9]=1[C:4](=[O:6])[CH:3]=[C:2]([S:1][CH:21]([CH3:26])[C:20]([OH:23])=[O:22])[C:13]2=[O:18]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 65143-Mercaptopropionic AcidHCID 8857Ethyl AcetateHCID 122809971,4-Naphthalenedione, 5-methyl-

Product 1

HCID 67851956HCID 67851956, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent2×HCID 962WaterSolvent

Procedure

3-Mercaptopropionic acid (0.69 mmol, 65 μL) was dissolved in 8 mL of water and cooled in an ice bath. This solution was added over 20-30 minutes to a solution of 5-methyl-1,4-naphthoquinone (0.69 mmole, 120 mg) dissolved in 15 mL of ethanol and cooled in an ice bath to form a reaction mixture. The reaction mixture was gradually allowed to warm to room temperature over a 1 hour period, and the ethanol was then allowed to evaporate. The crude product was purified via flash silica column chromatography (2:1 hexane:ethyl acetate with 1% v/v acetic acid) and provided a 70% yield of (5-methyl-1,4 naphthoquinonyl thio)- propionic acid, designated compound 1. 1H NMR data: (acetone-ds), δ 2.70 (s, 3H), 2.81 (t, J=7.2 Hz, 2H), 3.20 (t, J=7.2 Hz, 2H), 6.72 (s, 1H), 7.62 (d, J=7.5 Hz, 1H), 7.71 (t, J=7.5 Hz, 1H) 7.96 (d, J=Hz, 1H). LRMS m/z (rel. int.) 276 (M+, 30.5) 203 (100), 115 (68.2), 90 (41.0), 89 (76.4).

Workup

  1. temperaturecooled in an ice bath
  2. temperaturecooled in an ice bath
  3. customto form a reaction mixture
  4. customto evaporate
  5. customThe crude product was purified via flash silica column chromatography (2:1 hexane

Sources & evidence

ORD record
ord-37807fc0e68341e9b059ebddc34dca39
Source dataset
uspto-grants-1994_03
Patent number
US05292873

Reaction notes

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