Imidazole → HCID 89651613, compound

HRID 1479034Notes

Reaction equation

HRID 1479034 reaction equation
[C:1]([Si:5](Cl)([CH3:7])[CH3:6])([CH3:4])([CH3:3])[CH3:2].[OH:9][CH2:10][CH:11]([CH3:21])[O:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16].CCN(C(C)C)C(C)C.N1C=CN=C1>O1CCOCC1>[C:1]([Si:5]([CH3:7])([CH3:6])[O:9][CH2:10][CH:11]([CH3:21])[O:12][C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[CH:15]=[O:16])([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 81531DiisopropylethylamineHCID 57210661HCID 57210661, compound

Product 1

HCID 89651613HCID 89651613, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Tert-butyl-chloro-dimethyl-silane (649 mg; 4.3 mmol; 1.1 eq.) was added to a solution of 2-(2-hydroxy-1-methyl-ethoxy)-benzaldehyde (705 mg; 3.91 mmol; 1 eq.), DIEA (867 μL; 4.69 mmol; 1.2 eq.) and 1H-imidazole (27 mg; 0.39 mmol; 0.1 eq.) in 1,4-dioxane (20 mL) and the resulting mixture was stirred at room temperature for 10 minutes. After dilution with EA, the solution was washed with sat. aq. NH4Cl (3×), dried over magnesium sulfate and concentrated in vacuo. Purification by column chromatography (20% to 50% EA in cyclohexane) to afford the title compound (690 mg, 60%) as a colourless oil. 1H NMR (300 MHz, DMSO-d6) δ 10.47-10.33 (m, 1H), 7.72-7.55 (m, 2H), 7.30 (d, J=8.5 Hz, 1H), 7.05 (t, J=7.5 Hz, 1H), 4.71 (d, J=4.2 Hz, 1H), 3.77 (dd, J=4.8, 2.1 Hz, 2H), 1.28 (d, J=6.2 Hz, 3H), 0.84-0.75 (m, 9H), 0.04-0.07 (m, 6H).

Workup

  1. washAfter dilution with EA, the solution was washed with sat. aq. NH4Cl (3×)
  2. dry with materialdried over magnesium sulfate
  3. concentrationconcentrated in vacuo
  4. customPurification by column chromatography (20% to 50% EA in cyclohexane)

Sources & evidence

ORD record
ord-2b6ee560d8214714bf1bb6183e971283
Source dataset
uspto-grants-2016_08
Patent number
US09403835B2

Reaction notes

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