Ammonium Chloride → HCID 10829728, compound

HRID 565427Notes

Reaction equation

HRID 565427 reaction equation
[CH3:1]CC([O-])(C)C.[Na+].[I-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Br:29][C:30]1[CH:47]=[CH:46][CH:45]=[CH:44][C:31]=1[CH2:32][CH:33]1[C:42](=O)[CH2:41][CH2:40][C:35]2([O:39][CH2:38][CH2:37][O:36]2)[CH2:34]1.[NH4+].[Cl-]>C1(C)C=CC=CC=1>[Br:29][C:30]1[CH:47]=[CH:46][CH:45]=[CH:44][C:31]=1[CH2:32][CH:33]1[C:42](=[CH2:1])[CH2:41][CH2:40][C:35]2([O:39][CH2:38][CH2:37][O:36]2)[CH2:34]1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 638159Methyltriphenylphosphonium iodideHCID 2733478Sodium 2-methylbutan-2-olateHCID 10616009HCID 10616009, compound

Product 1

HCID 10829728HCID 10829728, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A solution of sodium tert-pentoxide (70 ml of a 1M solution), prepared for immediate use, is added to a suspension of methyl(triphenyl)phosphonium iodide (25 g, 61.8 mmol) in 50 ml of toluene, and the mixture is stirred at room temperature under nitrogen for 20 minutes. The compound obtained in Step 1 (6.70 g, 20.6 mmol) dissolved in 50 ml of toluene is added dropwise and the reaction mixture is refluxed for 3 hours. After cooling, the reaction mixture is hydrolysed with a saturated NH4Cl solution and extracted with ether. The organic phase is washed with a saturated NaCl solution, H2O, dried over MgSO4 and concentrated in vacuo. The title product is purified by flash chromatography over a column (SiO2, toluene/cyclohexane:60/40).

Workup

  1. additionis added dropwise
  2. temperaturethe reaction mixture is refluxed for 3 hours
  3. temperatureAfter cooling
  4. extractionextracted with ether
  5. washThe organic phase is washed with a saturated NaCl solution, H2O
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe title product is purified by flash chromatography over a column (SiO2, toluene/cyclohexane:60/40)

Sources & evidence

ORD record
ord-a18fe4027df2428386a4ee4a5197eb1e
Source dataset
uspto-grants-2001_01
Patent number
US06172097B2

Reaction notes

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