Methoxymethyl-triphenylphosphonium chloride → 4-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester

HRID 658305Notes

Reaction equation

HRID 658305 reaction equation
[Cl-].[CH3:2][O:3][CH2:4][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.CC(C)([O-])C.[K+].[CH3:30][O:31][C:32](=[O:47])[C:33]1[CH:38]=[CH:37][C:36]([C:39](=O)[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:34]=1>C1(C)C=CC=CC=1>[CH3:30][O:31][C:32](=[O:47])[C:33]1[CH:38]=[CH:37][C:36]([C:39](=[CH:2][O:3][CH3:4])[CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 23665647Potassium tert-butoxideHCID 598693704-Heptanoyl-benzoic acid methyl ester

Product 1

HCID 684911714-(1-Methoxymethylene-heptyl)-benzoic acid methyl ester

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

(Methoxymethyl)triphenylphosphonium chloride (10.34 g, 30.24 mmol) is suspended in anhydrous toluene (75 mL) and potassium tert-butoxide (3.39 g, 30.24 mmol) is carefully added. The solution is allowed to stir at room temperature for 4 h. 4-Heptanoyl-benzoic acid methyl ester (5.0 g, 20.16 mmol) is then dissolved in anhydrous toluene (25 mL) and added to the reaction mixture by cannula. The reaction is allowed to stir at room temperature overnight and is monitored by TLC. Upon complete consumption of starting material, the reaction is carefully quenched with saturated ammonium chloride solution, extracted with diethyl ether, washed, dried, and concentrated. The title compound is purified by column chromatography using hexanes/ethyl acetate and used directly in the next step.

Workup

  1. additionadded to the reaction mixture by cannula
  2. stirringto stir at room temperature overnight
  3. customUpon complete consumption of starting material
  4. customthe reaction is carefully quenched with saturated ammonium chloride solution
  5. extractionextracted with diethyl ether
  6. washwashed
  7. customdried
  8. concentrationconcentrated
  9. customThe title compound is purified by column chromatography

Sources & evidence

ORD record
ord-e627c22587b94daa994910e9c163ac31
Source dataset
uspto-grants-2011_12
Patent number
US08076374B2

Reaction notes

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