HCID 66577568, compound → HCID 66582146, compound

HRID 73625Notes

Reaction equation

HRID 73625 reaction equation
[CH2:1]([O:4][CH2:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[CH2:12])C=C>ClCCCl>[CH2:5]1[CH:6]2[C:7]([CH2:8][CH2:9][CH2:10][CH2:11]2)=[CH:12][CH2:1][O:4]1

Participants

3

Reactant 1

HCID 66577568HCID 66577568, compound

Product 1

HCID 66582146HCID 66582146, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of (2-methylidenecyclohexyl)methyl prop-2-en-1-yl ether (0.104 g, 0.626 mmol) in DCE (6.5 mL) was degassed 3×N2/pump, then Zhan-1b (0.023 g, 0.031 mmol) was added and the reaction was degassed again The mixture was stirred at rt for 2 hr. It was concentrated and purified by silica gel chromatography to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.39 (t, 1H, J=2.4 Hz), 4.04-4.10 (m, 2H), 3.92 (dd, 1H, J=5.7 Hz, 11.2 Hz), 3.24 (dd, 1H, J=8.2 Hz, 11.2 Hz), 2.15-2.27 (m, 2H), 1.92-2.02 (m, 1H), 1.74-1.83 (m, 2H), 1.64-1.72 (m, 1H), 1.18-1.45 (m, 2H), 0.93-1.06 (m, 1H).

Workup

  1. customwas degassed 3×N2/pump
  2. additionZhan-1b (0.023 g, 0.031 mmol) was added
  3. customthe reaction was degassed again The mixture
  4. concentrationIt was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-c80dd22759094004990e6930310fae21
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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