Benzaldehyde → HCID 54066443, compound

HRID 373571Notes

Reaction equation

[Br-].[CH3:2][N:3]1[C:12]2[C:7](=[CH:8][C:9]([CH:13]([P+](C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[CH3:14])=[CH:10][CH:11]=2)[C:6]([CH3:35])([CH3:34])[CH2:5][CH2:4]1.C([Li])CCC.[CH:41](=O)[C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1.CCCCCC>[CH3:2][N:3]1[C:12]2[C:7](=[CH:8][C:9]([C:13]([CH3:14])=[CH:41][C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)=[CH:10][CH:11]=2)[C:6]([CH3:34])([CH3:35])[CH2:5][CH2:4]1

Participants

Conditions

Temperature: -20 °C

Procedure

5.1 g of [1-(1,2,3,4-tetrahydro-1,4,4-trimethyl6-quinolinyl)ethyl]triphenylphosphonium bromide were suspended in 40 ml of tetrahydrofuran and treated at -20° C. with 5.9 ml of a 1.6 molar solution of n-butyllithium in hexane. After stirring at -20° C. for 1 hour, 1 g of benzaldehyde was added thereto and the mixture was stirred at room temperature for an additional 1 hour. After working-up in analogy to Example 49 and recrystallization from hexane, there were obtained 1.2 g of 1,2,3,4-tetrahydro-1,4,4-trimethyl-6-(α-methylstyryl)quinoline, melting point 69°-71° C.

Workup

stirringthe mixture was stirred at room temperature for an additional 1 hour
customAfter working-up in analogy to Example 49 and recrystallization from hexane

Sources & evidence

ORD record: ord-344199f226db47e1a5a4749456ae8eca
Source dataset: uspto-grants-1992_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05164387

Reaction notes

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