Hexafluoroacetone → HCID 22615244, compound

HRID 842730Notes

Reaction equation

HRID 842730 reaction equation
[F:1][C:2]([F:10])([F:9])[C:3]([C:5]([F:8])([F:7])[F:6])=[O:4].O[CH:12]([CH2:16][CH:17]1[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1)[C:13]([OH:15])=[O:14]>CS(C)=O.C(Cl)Cl.O>[F:1][C:2]([F:10])([F:9])[C:3]1([C:5]([F:8])([F:7])[F:6])[O:15][C:13](=[O:14])[CH:12]([CH2:16][CH:17]2[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]2)[O:4]1

Participants

5

Reactant 2

HCID 12695HexafluoroacetoneHCID 12756209HCID 12756209, compound

Product 1

HCID 22615244HCID 22615244, compound

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 21908982Water methylene chlorideSolvent

Procedure

2-Hydroxy-3-cyclohexylpropionic acid prepared as described in Step 2 (2.24 g, 13.0 mmol) was treated as described in J.Org. Chem., 1995, 60, 7641-7645 to provide [2,2-Bis(trifluoromethyl)-4-oxo-1,3-dioxolan-5-yl]methyl cyclohexane. Thus, a solution of hexafluoroacetone (27.3 mmol) in DMSO (5 mL) was added to 2-hydroxy-3-cyclohexylpropionic acid and the mixture stirred for 2 hours under a dry ice condenser. The mixture was then diluted with 100 mL of 1:1 methylene chloride/water and the aqueous layer extracted twice with methylene chloride. The combined organic layers were dried and concentrated to provide the title compound. 1H-NMR (CDCl3): 4.7 ppm (m, 1H); 1.6-1.9 ppm (m, 5H); 1.3 ppm (m, 3H); 0.95 ppm (m, 2H).

Workup

  1. extractionthe aqueous layer extracted twice with methylene chloride
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-c6f614251bac40fbb3b6af4c78c1bb59
Source dataset
uspto-grants-2002_04
Patent number
US06376496B1

Reaction notes

Loading…