4-Methyl-2-methylene valeric acid → 2-[(Acetylthio)methyl]-4-methylpentanoic acid

HRID 1636992Notes

Reaction equation

HRID 1636992 reaction equation
[CH3:1][CH:2]([CH3:9])[CH2:3][C:4](=[CH2:8])[C:5]([OH:7])=[O:6].[C:10]([OH:13])(=[S:12])[CH3:11]>>[CH3:1][CH:2]([CH3:9])[CH2:3][CH:4]([CH2:8][S:12][C:10](=[O:13])[CH3:11])[C:5]([OH:7])=[O:6]

Participants

3

Reactant 2

HCID 1686594-Methyl-2-methylene valeric acidHCID 178418634HCID 178418634, compound

Product 1

HCID 130175572-[(Acetylthio)methyl]-4-methylpentanoic acid

Conditions

Temperature
95 °C

Procedure

A mixture of 4-methyl-2-methylenepentanoic acid (5.0 g) and thioacetic acid (25 mL) was heated at 95° C. under argon for 3 days. The excess thioacetic acid was evaporated and the residual oil was dissolved in ethyl acetate (40 mL) and extracted with saturated NaHCO3 (3×40 mL). The combined NaHCO3 extracts were combined and acidified at 0° C. to pH 2 with 1M HCl. The aqueous layer was extracted with CHCl2 (3×40 mL), the combined organic phases were dried (MgSO4) and evaporated to give 3.0 g of 4-methyl-2-acetylthiomethyl-pentanoic acid; 1H NMR (80 MHz, CDCl3) δ 0.95 (d, J=8.0, 6H), 1.20-1.90 (m, 4H), 2.35 (s, 3H), 2.50-3.20 (m, 3H), 6.7 (br s, 1H).

Workup

  1. customThe excess thioacetic acid was evaporated
  2. dissolutionthe residual oil was dissolved in ethyl acetate (40 mL)
  3. extractionextracted with saturated NaHCO3 (3×40 mL)
  4. customacidified at 0° C. to pH 2 with 1M HCl
  5. extractionThe aqueous layer was extracted with CHCl2 (3×40 mL)
  6. dry with materialthe combined organic phases were dried (MgSO4)
  7. customevaporated

Sources & evidence

ORD record
ord-98fa2c6eead14708b4ec130c497c9cfc
Source dataset
uspto-grants-2000_03
Patent number
US06037472

Reaction notes

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