4-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime → [5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]methanol

HRID 1245402Notes

Reaction equation

HRID 1245402 reaction equation
[C:1]([SiH2:5][O:6][C:7]([CH3:13])([CH3:12])[C:8](=[CH2:11])[CH2:9][OH:10])([CH3:4])([CH3:3])[CH3:2].[CH3:14][C:15]1[CH:24]=[C:23]([CH2:25][O:26][C:27]2[CH:35]=[CH:34][C:30]([CH:31]=[N:32][OH:33])=[CH:29][CH:28]=2)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:16]=1>C1COCC1>[C:1]([SiH2:5][O:6][C:7]([CH3:13])([CH3:12])[C:8]1([CH2:9][OH:10])[O:33][N:32]=[C:31]([C:30]2[CH:29]=[CH:28][C:27]([O:26][CH2:25][C:23]3[C:22]4[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=4)[N:16]=[C:15]([CH3:14])[CH:24]=3)=[CH:35][CH:34]=2)[CH2:11]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 738530794-(2-Methyl-quinolin-4-ylmethoxy)-benzaldehyde oximeHCID 1317259963-Tert-butylsilyloxy-3-methyl-2-methylidenebutan-1-ol

Product 1

HCID 131725995[5-(2-tert-butylsilyloxypropan-2-yl)-3-[4-[(2-methylquinolin-4-yl)methoxy]phenyl]-4H-1,2-oxazol-5-yl]methanolYield 61%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of Clorox® was added dropwise (1 mL) to a solution of the product from step 24a (0.52 g, 2.56 mmol) and 4-(2-methyl-quinolin-4-ylmethoxy)-benzaldehyde oxime (0.5 g, 1.71 mmol) from step 1b in THF (4 mL) under nitrogen atmosphere at room temperature. The reaction was stirred overnight, partitioned between ethyl acetate and water saturated with KH2PO4. The organic layer was washed with brine, dried over magnesium sulfate, and concentrated to give an oil. The product was purified by FCC on silica gel eluting methylene chloride:ethyl acetate (50:50) to give {5-(tert-butyl-dimethyl-silanyloxymethyl)-3-[4-(2-methyl-quinolin-4-ylmethoxy)-phenyl]-4,5-dihydro-isoxazol-5-yl}-methanol (0.51 g, 61%) as an oil. MS found: (M+H)+=493.

Workup

  1. custompartitioned between ethyl acetate and water saturated with KH2PO4
  2. washThe organic layer was washed with brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customto give an oil
  6. customThe product was purified by FCC on silica gel
  7. washeluting methylene chloride:ethyl acetate (50:50)

Sources & evidence

ORD record
ord-cbc781d40af3484e995ca65ee7d17531
Source dataset
uspto-grants-2006_10
Patent number
US07125870B2

Reaction notes

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