Tetrahydrofuran → (S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

HRID 356529Notes

Reaction equation

HRID 356529 reaction equation
[OH:1][C@:2]([CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=1)([CH:7]([CH3:9])[CH3:8])[CH2:3][C:4]([OH:6])=O.C1N=CN(C(N2C=NC=C2)=O)C=1.C1C[O:34][CH2:33][CH2:32]1>>[OH:6][C:4]1[CH2:3][C@@:2]([CH2:10][CH2:11][C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)([CH:7]([CH3:9])[CH3:8])[O:1][C:33](=[O:34])[CH:32]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 53816519HCID 53816519, compound

Product 1

HCID 54682331(S)-4-hydroxy-6-[2-(4-hydroxy-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Procedure

The title compound was prepared using (S)-3-hydroxy-3-[2-(4-hydroxy-phenyl)-ethyl]-4-methyl-pentanoic acid (0.45 g, 1.78 mmol) from Example UUUU, THF (10 mL), and CDI (0.58 g, 3.58 mmol). The reaction was stirred overnight at room temperature then added to bis[3-ethoxy-3-oxopropanoato(1-)-O,O']-magnesate (1.5 g, 5.2 mmol) from Example VVVV and the reaction stirred for 3 days at room temperature. The reaction was concentrated and the residue partitioned between ethyl acetate and 1N HCl. The organic layer was washed with aqueous NaHCO3 and brine, dried (MgSO4) and concentrated.

Workup

  1. stirringthe reaction stirred for 3 days at room temperature
  2. concentrationThe reaction was concentrated
  3. customthe residue partitioned between ethyl acetate and 1N HCl
  4. washThe organic layer was washed with aqueous NaHCO3 and brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-575f1b44719f4ec092b8cbf2fa9f2cd3
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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