Ammonium Chloride → HCID 21097831, compound

HRID 1351102Notes

Reaction equation

HRID 1351102 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1Br)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])(C)(C)C.C([O:29][CH2:30][CH2:31][N:32]1[C:36]([CH:37]([CH3:39])[CH3:38])=[C:35]([CH:40]=[O:41])[C:34]([O:42][CH2:43][C:44]2[CH:49]=[CH:48][CH:47]=[CH:46][CH:45]=2)=[N:33]1)(=O)C1C=CC=CC=1.[Cl-].[NH4+]>O1CCCC1>[CH2:43]([O:42][C:34]1[C:35]([CH:40]([C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[O:8][CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[OH:41])=[C:36]([CH:37]([CH3:38])[CH3:39])[N:32]([CH2:31][CH2:30][OH:29])[N:33]=1)[C:44]1[CH:45]=[CH:46][CH:47]=[CH:48][CH:49]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5618281-(Benzyloxy)-2-bromobenzeneHCID 22932185HCID 22932185, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 21097831HCID 21097831, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-benzyloxybromobenzene (1.66 g) in tetrahydrofuran (50 mL) was added tert-butyllithium (1.6 mol/L pentane solution, 4.33 mL) at −78° C. under an argon atmosphere, and the mixture was stirred for 5 minutes. To the reaction mixture was added a solution of 1-(2-benzoyloxyethyl)-3-benzyloxy-4-formyl-5-isopropyl-1H-pyrazole (620 mg) in tetrahydrofuran (5 mL), and the mixture was stirred at 0° C. for 30 minutes. To the reaction mixture was added a saturated aqueous ammonium chloride solution, and the resulting mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/1–2/1) to give 2-{3-benzyloxy-4-[(2-benzyloxyphenyl)hydroxymethyl]-5-isopropylpyrazol-1-yl}ethanol (448 mg). To a solution of 2-{3-benzyloxy-4-[(2-benzyloxyphenyl)hydroxymethyl]-5-isopropylpyrazol-1-yl}ethanol (448 mg) in methanol (5 mL) was added 10% palladium-carbon powder (448 mg), and the mixture was stirred at room temperature under a hydrogen atmosphere for 3 hours. The insoluble material was removed by filtration, and the solvent of the filtrate was removed under reduced pressure to give the title compound (220 mg).

Workup

  1. stirringthe mixture was stirred at 0° C. for 30 minutes
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (eluent: ethyl acetate/hexane=1/1–2/1)

Sources & evidence

ORD record
ord-7c07468079ac4727afa4ad79159a54fd
Source dataset
uspto-grants-2007_05
Patent number
US07217697B2

Reaction notes

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