Imidazole → HCID 6950526, compound

HRID 1511861Notes

Reaction equation

HRID 1511861 reaction equation
[CH3:1][C@H:2]1[CH2:4][O:3]1.C(N(CC)CC)C.[C:12]1([OH:18])[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C=CN=C1.C([Si](C(C)C)(C(C)C)Cl)(C)C>CN(C=O)C>[O:18]([CH2:1][C@@H:2]([OH:3])[CH3:4])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

7

Reactant 5

HCID 795ImidazoleHCID 996PhenolHCID 8471TriethylamineHCID 139400Triisopropylsilyl chlorideHCID 146262(2S)-2-Methyloxirane

Product 1

HCID 6950526HCID 6950526, compoundYield 108.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A microwave vessel was charged with (S)-2-methyl-oxirane (0.46 ml, 7.78 mmol), triethylamine (0.33 ml, 2.36 mmol), phenol (222 mg, 2.36 mmol) and DMF (2.0 ml). The mixture was heated by microwave for 20 minutes at 150° C. The reaction was concentrated and dried under reduced pressure. The crude mixture (approximately 9:1) was dissolved in DMF (3.0 ml) and treated with imidazole (160 mg, 2.36 mmol) and Triisopropylchlorosilane (181 mg, 0.94 mmol) overnight at room temperature under nitrogen. The reaction was concentrated under reduced pressure and the crude product was purified via flash chromatography using 3:2/heptane:Ethyl acetate as eluant. Fractions containing product were combined and concentrated to afford (S)-1-Phenoxy-propan-2-ol (390 mg, 62%) as a clear oil.

Workup

  1. concentrationThe reaction was concentrated
  2. customdried under reduced pressure
  3. dissolutionThe crude mixture (approximately 9:1) was dissolved in DMF (3.0 ml)
  4. concentrationThe reaction was concentrated under reduced pressure
  5. customthe crude product was purified via flash chromatography
  6. additionFractions containing product
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8e0eab3f89284fcb839af765b10404d3
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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