Trifluoroacetic acid → (3R,4R,5S)-3-ethoxy-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]dihydrofuran-2(3H)-one

HRID 1670443Notes

Reaction equation

HRID 1670443 reaction equation
C(O)(C(F)(F)F)=O.[CH2:8]([O:10][C@@H:11]1[C@@H:15]2[O:16]C(C)(C)[O:18][C@H:19]([CH:20]=[CH2:21])[C@@H:14]2[O:13][C:12]1=[O:24])[CH3:9]>O>[CH2:8]([O:10][C@@H:11]1[C@H:15]([OH:16])[C@H:14]([C@H:19]([OH:18])[CH:20]=[CH2:21])[O:13][C:12]1=[O:24])[CH3:9]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 57617734(4R,4aS,7R,7aR)-7-ethoxy-2,2-dimethyl-4-vinyltetrahydro-6H-furo[3,2-d][1,3]dioxin-6-one

Product 1

HCID 57617787(3R,4R,5S)-3-ethoxy-4-hydroxy-5-[(1R)-1-hydroxyprop-2-en-1-yl]dihydrofuran-2(3H)-oneYield 82.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

2.8 ml of TFA are added to a 25 mL round-bottomed flask containing 13 mL of water and 800 mg of 50 (3.30 mmol). The medium is stirred for 2 h at RT and then the medium is diluted with 200 mL of water, frozen and freeze-dried. 550 mg of expected product 51 (flaky white solid) are obtained.

Workup

  1. temperaturefrozen
  2. customfreeze-dried

Sources & evidence

ORD record
ord-2646850d0e81485e8268cee249ad5258
Source dataset
uspto-grants-2011_08
Patent number
US07994161B2

Reaction notes

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