Methyltriphenylphosphonium iodide → HCID 18782830, compound

HRID 1420792Notes

Reaction equation

HRID 1420792 reaction equation
[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[CH3:22][C:23]([CH3:26])([O-])[CH3:24].[K+].C(C1[CH:36]([C:37]#[N:38])[CH2:35][CH:34]2[CH2:39][CH:32]1[C:33]2([CH3:41])[CH3:40])(=O)C>C1COCC1>[C:23]([CH:26]1[CH:36]([C:37]#[N:38])[CH2:35][CH:34]2[CH2:39][CH:32]1[C:33]2([CH3:41])[CH3:40])([CH3:24])=[CH2:22]

Participants

5

Reactant 3

HCID 638159Methyltriphenylphosphonium iodideHCID 18782828HCID 18782828, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 18782830HCID 18782830, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Methyltriphenylphosphonium iodide (3.17 g, 7.84 mmol) was suspended in anhydrous THF (20 ml) under an atmosphere of dry N2. To this solution was added a 1.0 M solution of potassium tert-butoxide (7.84 ml) in THF. After the reaction has stirred at ambient temperature for 30 min, a solution of 2-acetyl-6,6-dimethyl-bicyclo[3.1.1]heptane-3-carbonitrile (1.00 g, 5.23 mmol), prepared in step A of example 42, dissolved in anhydrous THF (10 ml) was added to the reaction. After stirring for two hours, the reaction was then partitioned between ethyl ether and water. The ethyl ether layer was washed with brine, dried over MgSO4, filtered and concentrated under vacuum to give an oil which was chromatographed on silica gel using a gradient of neat hexanes to 10% ethyl acetate in hexanes to give 490 mg of the titled compound as an oil: C.I. m/z 190 [M+1]; 1H NMR (CDCl3)δ 4.82 (m, 2H), 2.82 (m, 2H), 2.10-2.28 (m, 3H), 1.93 (m, 2H), 1.75 (s, 3H), 1.33 (d, J=9.9 Hz, 1H), 1.23 (s, 3H), 0.93 (s, 3H), 0.80-0.87 (m, 2H).

Workup

  1. additionwas added to the reaction
  2. stirringAfter stirring for two hours
  3. customthe reaction was then partitioned between ethyl ether and water
  4. washThe ethyl ether layer was washed with brine
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum
  8. customto give an oil which
  9. customwas chromatographed on silica gel using a gradient of neat hexanes to 10% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f893f07d14734b23aa299a84cbdb385b
Source dataset
uspto-grants-2000_06
Patent number
US06071935

Reaction notes

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