Iodoethane → (1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester

HRID 220460Notes

Reaction equation

[H-].[Na+].[CH2:3]([O:5][C:6](=[O:17])[CH2:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][NH:11][C:12]=1[CH2:13][CH3:14])[CH3:4].I[CH2:19][CH3:20]>O1CCCC1>[CH2:3]([O:5][C:6](=[O:17])[CH2:7][C:8]1[C:9]([CH2:15][CH3:16])=[N:10][N:11]([CH2:19][CH3:20])[C:12]=1[CH2:13][CH3:14])[CH3:4]

Participants

Conditions

Temperature: 0 °C

Procedure

Suspend sodium hydride (0.23 g, 5.71 mol, 60% dispersion in oil) in tetrahydrofuran (10 mL) and cool to 0° C. Add a solution of (3,5-diethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester (1.0 g, 4.76 mmol) in tetrahydrofuran (10 mL) dropwise. After stirring at 0° C. for 30 min., add iodoethane (0.46 mL, 5.71 mmol). Allow the reaction mixture to warm to room temperature while stirring for 18 hr. Partition between ethyl acetate (100 mL) and saturated aqueous ammonium chloride solution (50 mL). Separate the organic layer, dry (sodium sulfate), filter and concentrate to give (1,3,5-triethyl-1H-pyrazol-4-yl)-acetic acid ethyl ester as an oil (0.92 g, 81%). 1H-NMR (400 MHz, CDCl3) δ 4.09 (q, 2H), 4.01 (q, 2H), 3.33 (s, 2H), 2.58 (m, 4H), 1.38 (t, 3H), 1.20 (m, 9H).

Workup

temperatureto warm to room temperature
stirringwhile stirring for 18 hr
customPartition between ethyl acetate (100 mL) and saturated aqueous ammonium chloride solution (50 mL)
customSeparate the organic layer
dry with materialdry (sodium sulfate)
filtrationfilter
concentrationconcentrate

Sources & evidence

ORD record: ord-0f7eb54fafff4b50a8af6bf0d410e0bc
Source dataset: uspto-grants-2012_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08202873B2

Reaction notes

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