Ammonium Chloride → HCID 90389379, compound

HRID 1526533Notes

Reaction equation

HRID 1526533 reaction equation
CC(C)([O-])C.[K+].Cl[CH2:8][CH:9]1[O:13][N:12]=[C:11]([CH:14]([F:16])[F:15])[CH2:10]1.[NH4+].[Cl-]>C1COCC1>[F:15][CH:14]([F:16])[C:11]1[CH:10]2[CH:9]([CH2:8]2)[O:13][N:12]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 23665647Potassium tert-butoxideHCID 90389374HCID 90389374, compound

Product 1

HCID 90389379HCID 90389379, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of potassium tert-butoxide (1.0 M in THF, 66.3 mL, 66.3 mmol) was added dropwise to a solution of 5-(chloromethyl)-3-(difluoromethyl)-4,5-dihydroisoxazole (16a rac, 9.0 g, 53.1 mmol) in THF (70 mL) at 0° C. The reaction mixture was stirred for 30 min, then aqueous saturated NH4Cl solution was added slowly. The mixture was extracted with Et2O (2×), and the combined organic extracts were dried over MgSO4. The filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (0-60% Et2O/pentane gradient) to give the title compound as an oil (5.29 g, 75% yield)

Workup

  1. extractionThe mixture was extracted with Et2O (2×)
  2. dry with materialthe combined organic extracts were dried over MgSO4
  3. concentrationThe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (0-60% Et2O/pentane gradient)

Sources & evidence

ORD record
ord-706c982f39a74463bfc177bb11c65822
Source dataset
uspto-grants-2015_07
Patent number
US09085576B2

Reaction notes

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