3-Pyridinecarboxaldehyde → HCID 54529674, compound

HRID 1600169Notes

Reaction equation

C1([Li])C=CC=CC=1.[Cl-].[CH3:9][O:10][CH2:11][P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[N:31]1[CH:36]=[CH:35][CH:34]=[C:33]([CH:37]=O)[CH:32]=1.[Cl-].[NH4+]>CCOCC>[CH3:9][O:10][CH:11]=[CH:37][C:33]1[CH:32]=[N:31][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: -50 °C

Procedure

Phenyllithium (111 ml of 1.8M solution in ether) was added dropwise to a stirred suspension of (methoxymethyl) triphenylphosphonium chloride (68.6 g) in dry ether (600 ml) at -50° C. The mixture was stirred at -50° C. for 2 hours and then allowed to reach 0° C. over 30 minutes. 3-Pyridinecarboxaldehyde (10.70 g) was added dropwise with stirring, and the mixture was stirred at room temperature for 18 hours. Anexcess of ammonium chloride solution was then added and the layers were separated. The aqueous layer was separated and washed with ether, and the organic layers were combined and dried (MgSO4). The solvent was evaporated and the residue was chromatographed on silica gel initially using ethyl acetate/hexane (1:4) as eluant. The polarity was gradually increased to ethyl acetate/hexane (1:1) to give the pure product as an oil(8.82 g) which was used directly in the next stage.

Workup

waitto reach 0° C. over 30 minutes
stirringwith stirring
stirringthe mixture was stirred at room temperature for 18 hours
customthe layers were separated
customThe aqueous layer was separated
washwashed with ether
dry with materialdried (MgSO4)
customThe solvent was evaporated
customthe residue was chromatographed on silica gel initially using ethyl acetate/hexane (1:4) as eluant
temperatureThe polarity was gradually increased to ethyl acetate/hexane (1:1)

Sources & evidence

ORD record: ord-1d8c109ff643453e9a42b13399165b9e
Source dataset: uspto-grants-1998_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05744488

Reaction notes

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