Water → HCID 22037332, compound

HRID 1167515Notes

Reaction equation

HRID 1167515 reaction equation
[CH3:1][Si](C)(C)[N-][Si](C)(C)C.[Na+].[CH3:11][C:12]([Si:15]([CH3:37])([CH3:36])[O:16][CH2:17][CH2:18][NH:19][N:20]=[C:21]([C:29]1[CH:34]=[CH:33][C:32](F)=[CH:31][CH:30]=1)[CH2:22][C:23]1[CH:28]=[CH:27]N=[CH:25][CH:24]=1)([CH3:14])[CH3:13].[CH:38]1([C:41](OC)=O)[CH2:40][CH2:39]1.O>C1COCC1>[CH:38]1([C:41]2[N:19]([CH2:18][CH2:17][O:16][Si:15]([C:12]([CH3:14])([CH3:13])[CH3:11])([CH3:37])[CH3:36])[N:20]=[C:21]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:22]=2[C:23]2[CH:28]=[CH:27][CH:1]=[CH:25][CH:24]=2)[CH2:40][CH2:39]1

Participants

6

Reactant 4

HCID 962WaterHCID 76122Methyl cyclopropanecarboxylateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86594249HCID 86594249, compound

Product 1

HCID 22037332HCID 22037332, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of sodium hexamethyldisilazide (4.2 mL, 1.0 M in THF) at 0° C. was added a solution of the compound prepared in step 2 (0.78 g, 0.002 mol) in 10 mL of dry THF dropwise. The dark brown solution was stirred at this temperature for 30 minutes. Then a solution of methyl cyclopropanecarboxylate (0.27 g, 0.0026 mol) in 5 mL of dry THF was added. The reaction mixture was allowed to warm up to room temperature and stirred for 3 hours. Water was added and the aqueous phase was extracted with ethyl acetate. The organic layer was washed with brine, dried over magnesium sulfate and filtered. The filtrate was concentrated and purified by chromatography on silica gel (ethyl acetate/hexane, 3:7) to give 0.30 g of product, 5-cyclopropyl-1-[2-[[(1,1-dimethylethyl) dimethylsilyl]oxy]ethyl]-3,4-diphenyl-1H-pyrazole, as a light yellow oil (35% yield), 1H NMR (CDCL3): δ 8.53 (m, 2H), 7.32 (m, 2H), 7.14 (d, J=5.6 Hz, 2H), 6.97 (m, 2H), 4.47 (t, J=4.8 Hz, 2H), 4.14 (t, J=4.8 Hz, 2H), 1.93 (m, 1H), 0.95 (m, 2H), 0.87 (s, 9H), 0.41(m, 2H); Anal. Calc'd For C25H32FN3OSi: C, 68.61; H, 7.37; N, 9.60. Found: C, 68.39; H, 7.81; N, 9.23.

Workup

  1. stirringstirred for 3 hours
  2. extractionthe aqueous phase was extracted with ethyl acetate
  3. washThe organic layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationThe filtrate was concentrated
  7. custompurified by chromatography on silica gel (ethyl acetate/hexane, 3:7)

Sources & evidence

ORD record
ord-1bc87d6cd7b342e39d927678a7972427
Source dataset
uspto-grants-2003_09
Patent number
US06617324B1

Reaction notes

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