Ethyl Acetate → HCID 18753700, compound

HRID 1838448Notes

Reaction equation

HRID 1838448 reaction equation
[Si]([O:8][CH:9]1[CH2:13][CH:12]([N:14]2[C:23]3[CH:22]=[CH:21][CH:20]=[C:19]([Cl:24])[C:18]=3[C:17]3=[N:25][O:26][C:27]([CH3:28])=[C:16]3[C:15]2=[O:29])[CH:11]=[CH:10]1)(C(C)(C)C)(C)C.N1C=CC=CC=1.N1C=CC=CC=1.C1COCC1.C([O-])(O)=O.[Na+].C(OCC)(=O)C>C1COCC1>[Cl:24][C:19]1[C:18]2[C:17]3[C:16](=[C:27]([CH3:28])[O:26][N:25]=3)[C:15](=[O:29])[N:14]([CH:12]3[CH2:13][CH:9]([OH:8])[CH:10]=[CH:11]3)[C:23]=2[CH:22]=[CH:21][CH:20]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 516892Sodium Bicarbonate2×HCID 18753706HCID 18753706, compoundHCID 67604884HCID 67604884, compound

Product 1

HCID 18753700HCID 18753700, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5-[4-(t-butyl-dimethylsilanyl-oxy)cyclopent-2-en-1-yl]-9-chloro-3-methyl-5H-isoxazolo[4,3-c]quinolin-4-one (3.4 g, 7.9 mmol) in THF (60 mL) was added HF pyridine/pyridine/THF (1:2:8; 50 mL). The mixture was stirred at r.t. for 6 hours. Solid NaHCO3 (6 g) and ethyl acetate (60 mL) were added. Aqueous NaHCO3 was then added until the reaction was quenched The layers were separated and the organic fraction was washed (brine, water, aqueous CuSO4), dried (Na2SO4), filtered and concentrated. Column chromatography (silica gel, hexanes/ethyl acetate, gradient) gave desired product (2.2 g, 88%). 1H NMR (CDCl3, 400 MHz) δ; 7.59 (d, 1H); 7.37 (t, 1H); 7.30 (d, 1H); 6.15 (m, 1H); 5.91 (m, 1H); 5.78 (broad, 1H); 4.82 (broad, 1H); 2.81 (s, 3H); 2.82 (m, 1H); 2.18 (m, 1H).

Workup

  1. customwas quenched The layers
  2. customwere separated
  3. washthe organic fraction was washed (brine, water, aqueous CuSO4)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b89515ca1f6c432ea1ba196c9b49161b
Source dataset
uspto-grants-2004_01
Patent number
US06673809B2

Reaction notes

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