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

HRID 1670414Notes

Reaction equation

HRID 1670414 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)-oneYield 94.4%

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 17 (4.38 mmol), 10 ml of water and 14 ml of THF. The medium is left to return to AT and stirred overnight. The medium is then concentrated at reduced pressure, at AT, and 50 ml of water are added, and the mixture is frozen and lyophilized. The lyophilizate is made into a paste in heptane, in the presence of a minimum amount of methanol, after the solvents have been evaporated off. 778 mg of expected product 18 (white solid) are obtained.

Workup

  1. waitThe medium is left
  2. concentrationThe medium is then concentrated at reduced pressure, at AT, and 50 ml of water
  3. additionare added
  4. temperaturethe mixture is frozen
  5. customafter the solvents have been evaporated off

Sources & evidence

ORD record
ord-61cd48c5046b47a29e1c664c3d7b3d71
Source dataset
uspto-grants-2011_08
Patent number
US07994162B2

Reaction notes

Loading…