Pyridine → HCID 11085130, compound

HRID 711527Notes

Reaction equation

HRID 711527 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-4707dfe2d8e8412ca5570d3f4646ff10
Source dataset
uspto-grants-2015_11
Patent number
US09181255B2

Reaction notes

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