Water → 724466-52-8

HRID 2235879Notes

Reaction equation

HRID 2235879 reaction equation
O[C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9](=[N:14][OH:15])[C:10]([F:13])([F:12])[F:11].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CCOC(/N=N/C(OCC)=O)=O.O>C1COCC1>[F:13][C:10]([F:11])([F:12])[C:9]1[C:3]2[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=2[O:15][N:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 136340075HCID 136340075, compound

Product 1

HCID 136029785724466-52-8Yield 100.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

To a solution of 1-(2,4-dihydroxyphenyl)-2,2,2-trifluoroethanone oxime (Example 70, 0.25 g, 1.13 mmol) in THF (15 mL) was added triphenylphosphine (0.63 g, 2.4 mmol) and the mixture was cooled to 0° C. A solution of DEAD (0.48 mL, 2.3 mmol) in THF (10 mL) was slowly added while the temperature was kept at 0° C., after which the reaction mixture was stirred at 0-5° C. for 4 h. Water (30 mL) was added and the mixture was extracted with EtOAc (3×). The combined organic phases were washed with water and brine, dried over Na2SO4, filtered, and concentrated under reduced pressure. Purification by silica gel chromatography (EtOAc/hexane (v/v) 1:10 to 3:2 gradient) gave 0.23 g of the title compound with minor impurities. The material was used without further purification. GC-MS [M+H]+: 204.

Workup

  1. customwas kept at 0° C.
  2. extractionthe mixture was extracted with EtOAc (3×)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customPurification by silica gel chromatography (EtOAc/hexane (v/v) 1:10 to 3:2 gradient)

Sources & evidence

ORD record
ord-4967d62c3d83428cab00cdfa32b6068b
Source dataset
uspto-grants-2010_05
Patent number
US07714004B2

Reaction notes

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