1-(But-3-en-1-yloxy)-2-methylidenecyclohexane → HCID 66577517, compound

HRID 73619Notes

Reaction equation

HRID 73619 reaction equation
[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[CH2:12])[CH2:2]C=C>ClCCCl>[O:5]1[CH:6]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:12][CH2:2][CH2:1]1

Participants

3

Reactant 1

HCID 665774631-(But-3-en-1-yloxy)-2-methylidenecyclohexane

Product 1

HCID 66577517HCID 66577517, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 1-(but-3-en-1-yloxy)-2-methylidenecyclohexane (5.21 g, 31.3 mmol) in DCE (313 mL) was degassed 3×N2/pump. Zhan-1b (1.15 g, 1.57 mmol) was then added and the reaction was degassed again. The reaction was stirred at rt for 2 hr. The reaction mixture was concentrated and the residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.48 (d, 1H, J=2.7 Hz), 3.90-3.96 (m, 2H), 3.50-3.60 (m, 1H), 2.18-2.34 (m, 2H), 2.02-2.08 (m, 1H), 1.84-1.99 (m, 2H), 1.76-1.83 (m, 1H), 1.66-1.74 (m, 1H), 1.15-1.43 (m, 3H).

Workup

  1. customwas degassed 3×N2/pump
  2. additionZhan-1b (1.15 g, 1.57 mmol) was then added
  3. customthe reaction was degassed again
  4. concentrationThe reaction mixture was concentrated
  5. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-b0191e41605348fc90331a9b7ded68c1
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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