Ethyl Acetate → HCID 86658158, compound

HRID 388373Notes

Reaction equation

HRID 388373 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:33])([F:32])[F:31])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]#[C:25][Si](C)(C)C)=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.[Cl-].[NH4+].C(OCC)(=O)C>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2([C:30]([F:32])([F:31])[F:33])[O:13][N:12]=[C:11]([C:14]3[C:23]4[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=4)[C:17]([C:24]#[CH:25])=[CH:16][CH:15]=3)[CH2:10]2)[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

6

Reactant 3

HCID 8857Ethyl AcetateHCID 25517Ammonium ChlorideHCID 67434381HCID 67434381, compound

Product 1

HCID 86658158HCID 86658158, compound

Reagents, catalysts & solvents 2

HCID 70681Tetrabutylammonium ChlorideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A solution of tetrabutylammonium chloride (1 M in THF, 2.25 ml) is slowly added to a solution of crude 5-(3,5-dichloro-phenyl)-5-trifluoromethyl-3-(4-trimethylsilanylethynyl-naphthalen-1-yl)-4,5-dihydro-isoxazole (step A) in THF (25 ml) at 5° C. After 3 hours at 5° C. a saturated solution of ammonium chloride and ethyl acetate are added. The organic phase is washed with a saturated aqueous solution of NaCl, dried over MgSO4 and concentrated in vacuo. The crude product is purified on a semi-preparative HPLC to yield 5-(3,5-dichloro-phenyl)-3-(4-ethynyl-naphthalen-1-yl)-5-trifluoromethyl-4,5-dihydro-isoxazole as a brown solid.

Workup

  1. washThe organic phase is washed with a saturated aqueous solution of NaCl
  2. dry with materialdried over MgSO4
  3. concentrationconcentrated in vacuo
  4. customThe crude product is purified on a semi-preparative HPLC

Sources & evidence

ORD record
ord-0b3a449c1e284263b18e7a4ce8a77dcf
Source dataset
uspto-grants-2013_02
Patent number
US08377942B2

Reaction notes

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