Imidazole → O-(t-Butyldimethylsilyl)-1-(2-naphthyl)-6-heptenol

HRID 1182502Notes

Reaction equation

HRID 1182502 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[CH:11]([OH:18])[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17].[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].N1C=CN=C1.CNC1C=CC=C(NC)N=1.C(N(CC)CC)C>ClCCl>[Si:19]([O:18][CH:11]([C:2]1[CH:3]=[CH:4][C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:1]=1)[CH2:12][CH2:13][CH2:14][CH2:15][CH:16]=[CH2:17])([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

7

Reactant 5

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 111943672-N,6-N-dimethylpyridine-2,6-diamineHCID 230723861-(2-Naphthyl)-6-heptenol

Product 1

HCID 23072469O-(t-Butyldimethylsilyl)-1-(2-naphthyl)-6-heptenolYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of alcohol 181 (1.0 g, 4.16 mmol) in dichloromethane (40 mL) at room temperature under nitrogen atmosphere were successively added solid t-butyldimethylsilyl chloride (815 mg, 5.41 mmol), imidazole (340 mg, 4.99 mmol), and a catalytic amount of 2,6-dimethylaminopyridine. The mixture was stirred over 1 hour and triethylamine (696 μL, 4.99 mmol) was added. The mixture was stirred for 2 days. The reaction was quenched with water and the layers separated. The aqueous layer was extracted with dichloromethane and the combined organic layers were washed successively with a 1N HCl (2×10 mL), a saturated solution of sodium bicarbonate and brine, dried (MgSO4) and concentrated in vacuo. The crude residue was purified by flash chromatography using hexane as the eluent, and affording the title compound 182 in 84% yield (1.24 g). 1H NMR: (300 MHz, CDCl3) δ: 7.83-7.79 (m, 3H), 7.70 (s, 1H), 7.47-7.40 (m, 3H), 5.78 (ddt, J=17.0, 10.4, 6.6 Hz, 1H), 5.85-5.71 (m, 2H), 4.79 (dd, J=6.9, 4.9 Hz, 1H), 2.04-1.98 (m, 2H), 1.80-1.54 (m, 2H), 0.90 (s, 9H), 0.04 (s, 3H), −0.14 (s, 3H). MS (ESI)=223 (MH+-TBSO).

Workup

  1. customat room temperature
  2. stirringThe mixture was stirred for 2 days
  3. customThe reaction was quenched with water
  4. customthe layers separated
  5. extractionThe aqueous layer was extracted with dichloromethane
  6. washthe combined organic layers were washed successively with a 1N HCl (2×10 mL)
  7. dry with materiala saturated solution of sodium bicarbonate and brine, dried (MgSO4)
  8. concentrationconcentrated in vacuo
  9. customThe crude residue was purified by flash chromatography

Sources & evidence

ORD record
ord-0ec0d87e6d1f47b380875136dba92609
Source dataset
uspto-grants-2007_10
Patent number
US07288567B2

Reaction notes

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