Methyl 4-Formylbenzoate → Benzoic acid, 4-(1-hydroxy-3-phenyl-2-propynyl)-, methyl ester

HRID 129795Notes

Reaction equation

[C:1]1([C:7]#[C:8]C)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C([Li])CCC.[CH:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)=[O:16]>C1COCC1.CCCCCC>[OH:16][CH:15]([C:17]1[CH:26]=[CH:25][C:20]([C:21]([O:23][CH3:24])=[O:22])=[CH:19][CH:18]=1)[C:8]#[C:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of 4.40 mL (40.0 mmol) of phenylpropyne in 30 mL of THF under nitrogen at -75° C. was added a solution of 16 mL (40 mmol) of 2.5M n-butyllithium in hexane over 20 min. The resulting light yellow solution was warmed to 0° C. and stirred for 30 min. This solution was added via syringe to a slurry of 6.25 g (38.0 mmol) of methyl 4-formylbenzoate in 30 mL of THF at -30° C. over 20 min. The resulting light yellow solution was warmed to room temperature and stirred for 30 min. The reaction was quenched with saturated ammonium chloride solution, extracted twice with ether, dried (MgSO4) and evaporated. Purification by flash chromato-graphy (5×15 cm column, 1:19 ether/dichloromethane as elutent) gave title compound as a white solid, mp 48°-50° C., 9.36 g, 88% yield.

Workup

temperatureThe resulting light yellow solution was warmed to room temperature
stirringstirred for 30 min
customThe reaction was quenched with saturated ammonium chloride solution
extractionextracted twice with ether
dry with materialdried (MgSO4)
customevaporated
customPurification by flash chromato-graphy (5×15 cm column, 1:19 ether/dichloromethane as elutent)

Sources & evidence

ORD record: ord-4a1fb8a3b18f48cbb9114d75c266565a
Source dataset: uspto-grants-1995_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05470845

Reaction notes

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