Imidazole → HCID 85825706, compound

HRID 250534Notes

Reaction equation

HRID 250534 reaction equation
[CH3:1][CH:2]([CH2:7][CH2:8][CH3:9])[CH:3]([OH:6])[C:4]#[CH:5].N1C=CN=C1.[Si:15](Cl)([C:18]([CH3:21])([CH3:20])[CH3:19])([CH3:17])[CH3:16].[NH4+].[Cl-]>CN(C=O)C.CCOC(C)=O>[C:18]([Si:15]([CH3:17])([CH3:16])[O:6][CH:3]([CH:2]([CH3:1])[CH2:7][CH2:8][CH3:9])[C:4]#[CH:5])([CH3:21])([CH3:20])[CH3:19]

Participants

7

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 28928tert-Butyldimethylsilyl chlorideHCID 204420774-Methyl-1-heptyn-3-ol

Product 1

HCID 85825706HCID 85825706, compoundYield 97%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-methyl-hept-1-yn-3-ol (2.53 g, 0.02 mol) in dry DMF (25 mL) were added imidazole (1.63 g, 0.024 mol) and tert-butyldimethylsilyl chloride (3.62 g, 0.024 mol). The resulting solution was stirred at RT for 18 h and then treated with saturated NH4Cl (15 mL) and EtOAc (120 mL). The organic layer was washed with saturated NH4Cl (20 mL), water (4×20 mL), brine (2×20 mL), dried over sodium sulfate, and concentrated in vacuo to afford a crude product (4.65 g, 97%), as a yellow oil, which was used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.08 (s, 3H), 0.12 (s, 3H), 0.96-0.85 (m, 15H), 1.57-1.10 (m, 4H), 1.69-1.61 (m, 1H), 2.33 (t, J=2.20 Hz, 1H), 4.22-4.18 (m, 1H).

Workup

  1. washThe organic layer was washed with saturated NH4Cl (20 mL), water (4×20 mL), brine (2×20 mL)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d3310adf5e6a46779c2528003a09025b
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

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