Hydrochloric Acid → HCID 59492824, compound

HRID 1799036Notes

Reaction equation

HRID 1799036 reaction equation
C([O:5][C:6](=[O:32])[CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[C:25]3[C:24]4[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:18]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:17]=3[CH:16]=[C:15]([F:31])[CH:14]=2)[CH:10]=[N:9]1)(C)(C)C.[CH2:33]=[O:34].[F-].C([N+](CCCC)(CCCC)CCCC)CCC.Cl.CN(C)[CH:56]=[O:57]>O1CCCC1>[F:31][C:15]1[CH:14]=[C:13]([C:11]2[CH:10]=[N:9][N:8]([C:7]([CH2:56][OH:57])([CH2:33][OH:34])[C:6]([OH:5])=[O:32])[CH:12]=2)[C:25]2[C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[C:18]([OH:30])([C:26]([F:29])([F:28])[F:27])[C:17]=2[CH:16]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 6228DimethylformamideHCID 2724141Tetrabutylammonium FluorideHCID 59492525HCID 59492525, compound

Product 1

HCID 59492824HCID 59492824, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of an optically active form (33.3 g) of t-butyl[4-(2-fluoro-9-hydroxy-9-trifluoromethyl-9H-fluoren-4-yl)-pyrazol-1-yl]-acetate and paraformaldehyde (18.3 g) in dimethylformamide (100 ml) was added at room temperature a 1M solution (244 ml) of tetrabutylammonium fluoride in tetrahydrofuran, and the mixture was stirred at 90° C. for 4 hr. To the reaction mixture was added 1N hydrochloric acid (400 ml), and the mixture was extracted with ethyl acetate (200 ml). The separated aqueous layer was extracted twice with ethyl acetate (100 ml). The combined organic layer was successively washed once with 1N hydrochloric acid (100 ml), twice with brine (water/saturated brine=100 m1/10 ml) and once with saturated brine (100 ml), dried over anhydrous sodium sulfate and concentrated under reduced pressure. The obtained residue was azeotroped twice with toluene to give the title compound (28.3 g).

Workup

  1. extractionthe mixture was extracted with ethyl acetate (200 ml)
  2. extractionThe separated aqueous layer was extracted twice with ethyl acetate (100 ml)
  3. washThe combined organic layer was successively washed once with 1N hydrochloric acid (100 ml), twice with brine (water/saturated brine=100 m1/10 ml) and once with saturated brine (100 ml)
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe obtained residue was azeotroped twice with toluene

Sources & evidence

ORD record
ord-081ad954969144b0986be59466c1e8f7
Source dataset
uspto-grants-2013_01
Patent number
US08343994B2

Reaction notes

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