HCID 58938628, compound → HCID 58938674, compound

HRID 598102Notes

Reaction equation

[CH2:1]([Li])CCC.[CH2:6]([N:9]([CH2:32][CH2:33][CH3:34])[C:10]1[CH:11]=[C:12]([CH:30]=O)[C:13](=[O:29])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]1[C:25]([CH3:26])=[CH:24][C:23]([CH3:27])=[CH:22][C:21]=1[CH3:28])[CH2:7][CH3:8]>[Br-].C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O1CCCC1>[CH2:32]([N:9]([CH2:6][CH2:7][CH3:8])[C:10]1[CH:11]=[C:12]([CH:30]=[CH2:1])[C:13](=[O:29])[N:14]2[C:19]=1[CH:18]=[CH:17][CH:16]=[C:15]2[C:20]1[C:21]([CH3:28])=[CH:22][C:23]([CH3:27])=[CH:24][C:25]=1[CH3:26])[CH2:33][CH3:34]

Participants

Conditions

Temperature: 0 °C

Procedure

Methyltriphenylphosphonium bromide (0.46 g, 1.28 mmol) was suspended in tetrahydrofuran (10 mL). The solution was cooled to −78° C. n-Butyllithium (1.6M, 0.80 μL, 1.28 mmol) was added. After 0.5 h, the solution was warmed to 0° C. and stirred for an addition 0.5 h. The solution was cooled again to −78° C. and 1-(dipropylamino)-6-mesityl-4-oxo-4H-quinolizine-3-carbaldehyde (A) (0.050 g, 0.128 mmol) was added dropwise as a solution in tetrahydrofuran (0.5 mL). The reaction was warmed to −30° C. for 0.5 h. The reaction was quenched with water, extracted with ethyl acetate, dried, and concentrated. Flash chromatography (15% ethyl acetate/hexanes) gave the desired alkene (0.022 g, 45% yield) as a red oil.

Workup

additionwas added
temperatureThe solution was cooled again to −78° C.
temperatureThe reaction was warmed to −30° C. for 0.5 h
customThe reaction was quenched with water
extractionextracted with ethyl acetate
customdried
concentrationconcentrated

Sources & evidence

ORD record: ord-182905be947344b99f848960696ba1a7
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897607B2

Reaction notes

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