Tetrahydrofuran → 1-(But-3-en-1-yloxy)-2-methylidenecyclohexane

HRID 73618Notes

Reaction equation

HRID 73618 reaction equation
[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=O)[CH2:2][CH:3]=[CH2:4].[CH2:13]1COCC1>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH2:1]([O:5][CH:6]1[CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[CH2:13])[CH2:2][CH:3]=[CH2:4]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 665774622-(But-3-en-1-yloxy)cyclohexanone

Product 1

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

Reagents, catalysts & solvents 1

HCID 74505Methyltriphenyliphosphonium bromideCatalyst

Conditions

Temperature
60 °C

Procedure

To a mixture of methyltriphenylphosphonium bromide (22.30 g, 62.4 mmol) in THF (125 mL) at rt was added sodium hexamethyldisilylazide (2M in THF, 31.2 mL, 62.4 mmol) dropwise. The mixture was heated to 60° C. for 1 hr. 2-(but-3-en-1-yloxy)cyclohexanone (7.0 g, 41.6 mmol.) was then added and the mixture was stirred at 60° C. for 3 hr. The reaction was cooled to rt, quenched with sat'd. aq.NH4Cl, and extracted with Et2O. The combined organics were dried filtered, and concentrated. The residue was purified by column chromatography to give the title compound. 1H NMR (500 MHz, CDCl3) δ 5.78-5.90 (m, 1H), 5.00-5.13 (m, 2H), 4.82 (s, 1H), 4.78 (s, 1H), 3.74 (dd, 1H, J=3.9 Hz, 6.3 Hz), 3.35-3.49 (m, 2H), 1.12-2.38 (m, 10H).

Workup

  1. temperatureThe reaction was cooled to rt
  2. customquenched with sat'd
  3. extractionNH4Cl, and extracted with Et2O
  4. customThe combined organics were dried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-90c34293f49c4dff81dd74c6f9a27e52
Source dataset
uspto-grants-2014_09
Patent number
US08829196B2

Reaction notes

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