Imidazole → HCID 67958400, compound

HRID 527579Notes

Reaction equation

HRID 527579 reaction equation
N1C=CN=C1.Cl[Si:7]([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH3:14][O:15][CH2:16][O:17][C:18]1[CH:19]=[C:20]([CH2:24][OH:25])[CH:21]=[CH:22][CH:23]=1>ClCCl>[CH3:11][C:10]([Si:7]([CH3:9])([CH3:8])[O:25][CH2:24][C:20]1[CH:21]=[CH:22][CH:23]=[C:18]([O:17][CH2:16][O:15][CH3:14])[CH:19]=1)([CH3:13])[CH3:12]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12955823[3-(Methoxymethoxy)phenyl]methanol2×

Product 1

HCID 67958400HCID 67958400, compoundYield 102.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 100 ml round-bottomed flask (3-{[(methyloxy)methyl]oxy}phenyl)methanol (Intermediate 95, 3.5 g) was dissolved in dichloromethane (20 ml) to give a colourless solution. 1H-imidazole (1.700 g, 24.97 mmol) and chloro(1,1-dimethylethyl)dimethylsilane (3.64 g, 24.14 mmol) were added. The reaction mixture immediately became a white suspension and was stirred at room temperature. After overnight stirring the reaction was completed. The reaction mixture was then quenched with 10 ml of water and diluted with 10 ml of dichloromethane. The phases were separated through a separating funnel. The organic phase was dried using a hydrophobic frit and evaporated under vacuum to give 6.0082 g of the crude product as a colourless oil which was purified via Biotage SP1 (with cyclohexane/EtOAc as eluents from 1:0 to 5:1 in 10 CV; then 5:1 for 5 CV; then from 5:1 to 1:1 in 5 CV; 100 g SNAP Silica column). Two fractions of the title compound were collected: 1.70 g of a colourless oil (purity: 93%) and 3.70 g of a colourless oil (purity: 98%).

Workup

  1. customto give a colourless solution
  2. stirringAfter overnight stirring the reaction
  3. customThe reaction mixture was then quenched with 10 ml of water
  4. additiondiluted with 10 ml of dichloromethane
  5. customThe phases were separated through a separating funnel
  6. customThe organic phase was dried
  7. customevaporated under vacuum

Sources & evidence

ORD record
ord-7acd150b8c8342c1b4b155cd119d3a85
Source dataset
uspto-grants-2016_05
Patent number
US09346790B2

Reaction notes

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