(R)-3-hydroxymethylheptanoic acid, (S)-1-phenylethylamide → (R)-4-butyldihydrofuran-2-one

HRID 273196Notes

Reaction equation

HRID 273196 reaction equation
C1([C@@H](N[C:10](=[O:19])[CH2:11][C@H:12]([CH2:17][OH:18])[CH2:13][CH2:14][CH2:15][CH3:16])C)C=CC=CC=1>OS(O)(=O)=O.O1CCOCC1>[CH2:13]([C@H:12]1[CH2:17][O:18][C:10](=[O:19])[CH2:11]1)[CH2:14][CH2:15][CH3:16]

Participants

3

Reactant 1

HCID 86592431(R)-3-hydroxymethylheptanoic acid, (S)-1-phenylethylamide

Product 1

HCID 11217313(R)-4-butyldihydrofuran-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 19613996Dioxane sulfuric acidSolvent

Procedure

(R)-3-Hydroxymethylheptanoic acid, (S)-1-phenylethylamide (8.4 g, 31.9 mmol) was dissolved in 1 M H2SO4/dioxane (1:1, 110 mL) and the resulting solution was refluxed overnight under argon. After cooling to rt, the reaction mixture was diluted with ethyl acetate/hexanes (1:3, 200 mL) and washed with water (2×100 mL), saturated aq. NaHCO3 (2×100 mL), and brine (100 mL). The solution was dried (Na2SO4), filtered, and concentrated to afford pure (R)-4-butyldihydrofuran-2-one as a colorless oil (3.5 g, 78%).

Workup

  1. temperaturethe resulting solution was refluxed overnight under argon
  2. washwashed with water (2×100 mL), saturated aq. NaHCO3 (2×100 mL), and brine (100 mL)
  3. dry with materialThe solution was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-1476592dc3d8407cb80595a3968ee663
Source dataset
uspto-grants-2008_11
Patent number
US07456211B2

Reaction notes

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