Imidazole → 2-Fluoro-5-methoxy-3-(2-triisopropylsilanyloxyethoxymethyl)benzaldehyde

HRID 1161581Notes

Reaction equation

HRID 1161581 reaction equation
[F:1][C:2]1[C:9]([CH2:10][O:11][CH2:12][CH2:13][OH:14])=[CH:8][C:7]([O:15][CH3:16])=[CH:6][C:3]=1[CH:4]=[O:5].N1C=CN=C1.Cl[Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25].O>CN(C=O)C>[F:1][C:2]1[C:9]([CH2:10][O:11][CH2:12][CH2:13][O:14][Si:23]([CH:30]([CH3:32])[CH3:31])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])=[CH:8][C:7]([O:15][CH3:16])=[CH:6][C:3]=1[CH:4]=[O:5]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 139400Triisopropylsilyl chlorideHCID 595168732-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehyde

Product 1

HCID 595172852-Fluoro-5-methoxy-3-(2-triisopropylsilanyloxyethoxymethyl)benzaldehydeYield 103.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

2-Fluoro-3-(2-hydroxyethoxymethyl)-5-methoxybenzaldehyde (305 mg) was dissolved in 3 ml of DMF, and 300 mg of imidazole and 283 mg of chlorotriisopropylsilane were added thereto. The resulting mixture was stirred at 50° C. for 2 hours, and then water was added thereto. The mixture was extracted with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate. The desiccating agent was removed by filtration, and the filtrate was concentrated under reduced pressure to give a crude product of the title compound (533 mg).

Workup

  1. extractionThe mixture was extracted with ethyl acetate
  2. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  3. customThe desiccating agent was removed by filtration
  4. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-59dfd01664a446e8b6cb5dfd144219f5
Source dataset
uspto-grants-2010_10
Patent number
US07816522B2

Reaction notes

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