Water → (3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one

HRID 1670427Notes

Reaction equation

HRID 1670427 reaction equation
C(O)(C(F)(F)F)=O.[CH3:8][O:9][C@@H:10]1[C@@H:14]2[O:15]C(C)(C)[O:17][C@H:18]([CH:19]=[CH2:20])[C@@H:13]2[O:12][C:11]1=[O:23].O>C1COCC1>[OH:15][C@@H:14]1[C@H:13]([C@H:18]([OH:17])[CH:19]=[CH2:20])[O:12][C:11](=[O:23])[C@@H:10]1[O:9][CH3:8]

Participants

5

Reactant 3

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 49871274(4R,4aS,7R,7aR)-7-methoxy-2,2-dimethyl-4-vinyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one

Product 1

HCID 67241097(3R,4R,5S)-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]-3-methoxydihydrofuran-2(3H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

10 mL of TFA are added dropwise at 0° C. to a 100 mL round-bottomed flask containing 1.0 g of 30 (4.38 mmol), 10 mL of water and 14 mL of THF. The medium is allowed to return to RT and stirred overnight. The medium is then concentrated at reduced pressure at RT and 50 mL of water are added, and the mixture is frozen and freeze-dried. The freeze-dried product is impasted in heptane in the presence of a minimum amount of methanol, and after evaporation of the solvents, 778 mg of expected product 31 (white solid) are obtained.

Workup

  1. customto return to RT
  2. concentrationThe medium is then concentrated at reduced pressure at RT
  3. addition50 mL of water are added
  4. temperaturethe mixture is frozen
  5. customfreeze-dried
  6. customafter evaporation of the solvents, 778 mg of expected product 31 (white solid)
  7. customare obtained

Sources & evidence

ORD record
ord-166fd210f5344b15a6f81c90e95b9c23
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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