Imidazole → 2-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]furan

HRID 966895Notes

Reaction equation

HRID 966895 reaction equation
[OH:1][CH2:2][CH2:3][C:4]1[O:5][CH:6]=[CH:7][CH:8]=1.N1C=CN=C1.[CH3:14][C:15]([Si:18](Cl)([CH3:20])[CH3:19])([CH3:17])[CH3:16].C(OCC)C>CN(C=O)C>[CH3:14][C:15]([Si:18]([CH3:20])([CH3:19])[O:1][CH2:2][CH2:3][C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 3283Diethyl EtherHCID 28928tert-Butyldimethylsilyl chlorideHCID 6421102-Furanethanol

Product 1

HCID 218750272-[2-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]ethyl]furan

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

2-(2-Hydroxyethyl)furan (1.00 g, 8.93 mmol, Example 255A) was dissolved in DMF at 25° C. and imidazole (0.790 g, 11.6 mmol) was added. TBSCl (1.35 g, 8.93 mmol) was then added in portions over 5 minutes. After 2 h, the reaction was poured into diethyl ether (300 mL) and washed sequentially with water (1×100 mL), 1 N HCl (1×100 mL), and brine (1×100 mL). The combined organics were then dried over magnesium sulfate and concentrated in vacuo. Compound 241A was isolated as a clear oil (1.77 g) and was taken on without purification. HPLC: 100% at 4.233 min (retention time) (YMC S5 ODS column 4.6×50 mm, 10-90% aqueous methanol over 4 minutes containing 0.2% phosphoric acid, 4 mL/min, monitoring at 220 nm).

Workup

  1. washwashed sequentially with water (1×100 mL), 1 N HCl (1×100 mL), and brine (1×100 mL)
  2. dry with materialThe combined organics were then dried over magnesium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-e552ea7ce69d4742a1759b5e2cbb626f
Source dataset
uspto-grants-2005_10
Patent number
US06953679B2

Reaction notes

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