Pyridine → HCID 11085130, compound

HRID 2092831Notes

Reaction equation

HRID 2092831 reaction equation
N1C=CC=CC=1.[Si:7](Cl)([C:10]([CH3:13])([CH3:12])[CH3:11])([CH3:9])[CH3:8].[CH:15]1([OH:21])[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1>C(Cl)Cl>[C:10]([Si:7]([O:21][CH:15]1[CH2:20][CH2:19][CH2:18][CH:17]=[CH:16]1)([CH3:9])[CH3:8])([CH3:13])([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 1049PyridineHCID 131982-Cyclohexen-1-OLHCID 28928tert-Butyldimethylsilyl chloride

Product 1

HCID 11085130HCID 11085130, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Pyridine (4.74 g, 60 mmol) and tert-butyldimethylsilyl chloride (4.83 g, 32 mmol) were added to a solution of cyclohex-2-enol (1.96 g, 20 mmol) in DCM (40 mL). The reaction mixture was stirred at RT overnight. The mixture was concentrated and the residue was dispersed in EtOAc and water. The organic phase was separated and washed with brine, dried over anhydrous Na2SO4, concentrated, and purified by silica flash chromatography eluting with EtOAc and petroleum ether (5-10% EtOAc) to give the title compound as an oil (4.1 g, 97%). 1H NMR (400 MHz, CDCl3) δ ppm 0.06-0.09 (m, 6H), 0.92 (s, 9H), 1.50-1.57 (m, 2H), 1.74-1.89 (m, 2H), 1.93-2.03 (m, 2H), 4.21-4.23 (m, 1H), 5.61-5.64 (m, 1H), 5.72-5.76 (m, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. additionthe residue was dispersed in EtOAc
  3. customThe organic phase was separated
  4. washwashed with brine
  5. dry with materialdried over anhydrous Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica flash chromatography
  8. washeluting with EtOAc and petroleum ether (5-10% EtOAc)

Sources & evidence

ORD record
ord-c9b48cffefe3464ca4a6e0d81db192f9
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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