Methoxymethyl-triphenylphosphonium chloride → HCID 67341559, compound

HRID 1669244Notes

Reaction equation

HRID 1669244 reaction equation
CC(C)([O-])C.[K+].[Cl-].[CH3:8][O:9][CH2:10][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[F:30][C:31]([F:49])([F:48])[C:32]1[CH:37]=[CH:36][C:35]([C:38]2[CH:43]=[CH:42][C:41]([C:44](=O)[CH2:45][CH3:46])=[CH:40][CH:39]=2)=[CH:34][CH:33]=1>C1(C)C=CC=CC=1>[CH3:8][O:9][CH:10]=[C:44]([C:41]1[CH:42]=[CH:43][C:38]([C:35]2[CH:36]=[CH:37][C:32]([C:31]([F:49])([F:48])[F:30])=[CH:33][CH:34]=2)=[CH:39][CH:40]=1)[CH2:45][CH3:46]

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23005147HCID 23005147, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 67341559HCID 67341559, compoundYield 25.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a an ambient temperature suspension of potassium tert-butoxide (670 mg, 5.39 mmol) in toluene (36 mL) is added (methoxymethyl)triphenylphosphonium chloride (1.85 g, 5.56 mmol) and is stirred at room temperature for 30 min. 1-(4′-trifluoromethylbiphenyl-4-yl)-propan-1-one (1 g, 3.59 mmol) is added, and the reaction mixture continues to stir at room temperature overnight. The reaction mixture is filtered, using dichloromethane to aid rinsing, concentrated to ⅓ volume, then loaded onto silica gel and eluted using hexanes with an ethyl acetate gradient from 0% to 25% giving 4-(1-methoxymethylene-propyl)-4′-trifluoromethylbiphenyl (278 mg).

Workup

  1. stirringto stir at room temperature overnight
  2. filtrationThe reaction mixture is filtered
  3. washto aid rinsing
  4. concentrationconcentrated
  5. washeluted

Sources & evidence

ORD record
ord-b297af038ab049fa959286f632b390c1
Source dataset
uspto-grants-2011_08
Patent number
US07989457B2

Reaction notes

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