Carbon Tetrachloride → HCID 44184988, compound

HRID 2220237Notes

Reaction equation

HRID 2220237 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[C:5]([OH:25])([C:21]([F:24])([F:23])[F:22])[CH2:6][C:7]([C:10]1[CH:15]=[C:14]([F:16])[CH:13]=[C:12]([CH2:17][CH2:18]O)[C:11]=1[OH:20])([CH3:9])[CH3:8])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.C(Cl)(Cl)(Cl)Cl>C(#N)C>[CH2:1]([O:3][C:4](=[O:26])[C:5]([OH:25])([C:21]([F:23])([F:22])[F:24])[CH2:6][C:7]([C:10]1[C:11]2[O:20][CH2:18][CH2:17][C:12]=2[CH:13]=[C:14]([F:16])[CH:15]=1)([CH3:9])[CH3:8])[CH3:2]

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 58653729HCID 58653729, compound

Product 1

HCID 44184988HCID 44184988, compoundYield 89.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4-(5-Fluoro-2-hydroxy-3-(2-hydroxyethyl)phenyl)-2-hydroxy-4-methyl-2-trifluoromethyl-valeric acid ethyl ester (3.90 g, 10.2 mmol) is dissolved with triphenylphosphine (3.14 g, 12 mmol) and triethylamine (2.1 ml, 15 mmol) in acetonitrile (150 ml), mixed with carbon tetrachloride (2 ml) and stirred for 3 days in a nitrogen atmosphere at room temperature. The solvent is distilled off in a rotary evaporator, and the residue is taken up in ethyl acetate (150 ml) and water (75 ml). The ethyl acetate phase is separated, washed with saturated NaCl solution, dried (Na2SO4) and concentrated by evaporation in a vacuum. Column chromatography on silica gel with hexane-ethyl acetate yields 3.31 g of the product.

Workup

  1. distillationThe solvent is distilled off in a rotary evaporator
  2. customThe ethyl acetate phase is separated
  3. washwashed with saturated NaCl solution
  4. dry with materialdried (Na2SO4)
  5. concentrationconcentrated by evaporation in a vacuum

Sources & evidence

ORD record
ord-6bd5bd39716c4934b4bf8821a53f5aa1
Source dataset
uspto-grants-2008_08
Patent number
US07417056B2

Reaction notes

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