HCID 66577591, compound → HCID 66579282, compound

HRID 73637Notes

Reaction equation

HRID 73637 reaction equation
C=[C:2]1[CH2:7][CH2:6][O:5][CH2:4][CH:3]1[CH2:8][CH2:9][CH2:10][CH:11]=C>C(Cl)Cl>[CH2:4]1[CH:3]2[C:2](=[CH:11][CH2:10][CH2:9][CH2:8]2)[CH2:7][CH2:6][O:5]1

Participants

3

Reactant 1

HCID 66577591HCID 66577591, compound

Product 1

HCID 66579282HCID 66579282, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-methylidene-3-(pent-4-en-1-yl)tetrahydro-2H-pyran (0.198 g, 1.19 mmol) in CH2Cl2 (20 mL) was degassed (3×N2/pump). Zhan-Ib (0.044 g, 0.060 mmol) was added, the reaction was degassed again, and stirred at rt for 1 hr. The resulting mixture was concentrated and purified by silica gel chromatography to provide the title compound. 1H NMR (500 MHz, CDCl3) δ 5.47 (s, 1H), 3.90-4.10 (m, 2H), 3.26-3.35 (m, 1H), 2.94 (t, 1H, J=11.0 Hz), 2.24-2.40 (m, 2H), 1.74-2.07 (m, 3H), 1.65-1.76 (m, 2H), 1.38-1.49 (m, 1H), 0.96-1.07 (m, 1H).

Workup

  1. customwas degassed (3×N2/pump)
  2. additionZhan-Ib (0.044 g, 0.060 mmol) was added
  3. customthe reaction was degassed again
  4. concentrationThe resulting mixture was concentrated
  5. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-e830e878ad2b4b7b997fd5597a768d26
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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