Imidazole → HCID 89748843, compound

HRID 593401Notes

Reaction equation

HRID 593401 reaction equation
[C:1]1([CH2:7][CH2:8][C@H:9]([OH:12])[CH:10]=[CH2:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.N1C=CN=C1.[C:18]([Si:22](Cl)([CH3:24])[CH3:23])([CH3:21])([CH3:20])[CH3:19]>C(Cl)Cl>[C:18]([Si:22]([CH3:24])([CH3:23])[O:12][C@@H:9]([CH2:8][CH2:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)[CH:10]=[CH2:11])([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 9920461HCID 9920461, compound

Product 1

HCID 89748843HCID 89748843, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of allylic alcohol 66 (3.00 g, 18.5 mmol) in CH2Cl2 (53 ml) was cooled to 0° C. Imidazole (2.27 g, 33.3 mmol) was added in one portion followed by t-butylchlorodimethylsilane (3.34 g, 22.2 mmol). The cooling bath was removed and the reaction mixture stirred at r.t. for 16 h before being poured into 10% aq. HCl (100 ml). The mixture was extracted with 40/60 petroleum ether (2×100 ml). The combined organics were washed with saturated NaCl solution (100 ml), dried (MgSO4), filtered, and concentrated to give the crude material. This was purified by column chromatography, eluting with 40/60 petroleum ether, to give the protected alcohol 67 (4.68 g, 92%) as a colourless liquid. The 1H NMR data and optical rotation matched that reported in the literature (Uenishi, J. i. et al., Organic Letters 2011, 13, 2350).

Workup

  1. customThe cooling bath was removed
  2. additionbefore being poured into 10% aq. HCl (100 ml)
  3. extractionThe mixture was extracted with 40/60 petroleum ether (2×100 ml)
  4. washThe combined organics were washed with saturated NaCl solution (100 ml)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude material
  9. customThis was purified by column chromatography
  10. washeluting with 40/60 petroleum ether

Sources & evidence

ORD record
ord-d1e9be12b0074dcd943cf6b48eb3fbea
Source dataset
uspto-grants-2016_01
Patent number
US09242954B2

Reaction notes

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