4-Cyanobenzaldehyde → HCID 70112805, compound

HRID 989257Notes

Reaction equation

C([Li])CCC.[Si:6]([C:13]1[N:14]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[CH:15]=[CH:16][N:17]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7].[C:24]([C:26]1[CH:33]=[CH:32][C:29]([CH:30]=[O:31])=[CH:28][CH:27]=1)#[N:25].C([O-])(O)=O.[Na+]>C1COCC1>[Si:6]([C:13]1[N:14]([S:18]([N:21]([CH3:23])[CH3:22])(=[O:20])=[O:19])[C:15]([CH:30]([C:29]2[CH:32]=[CH:33][C:26]([C:24]#[N:25])=[CH:27][CH:28]=2)[OH:31])=[CH:16][N:17]=1)([C:9]([CH3:12])([CH3:11])[CH3:10])([CH3:8])[CH3:7]

Participants

Conditions

Temperature: -78 °C

Procedure

12.5 ml (19.9 mmol) of a solution of n-butyllithium (1.6M solution in hexane) are added slowly to a solution of the compound obtained in Step B (4.67 g, 18 mmol) in 40 ml of anhydrous THF that has been brought to −78° C., and then the whole is maintained at that temperature for 1 hour 30 minutes. A solution of p-cyanobenzaldehyde in 20 ml of THF, 3.3 g (25.1 mmol) is then added. The whole is stirred at −78° C. for 0.5 hour, and then hydrolysed with an aqueous saturated NaHCO3 solution. When the reaction mixture is at room temperature, it is extracted with AcOEt and then washed with a saturated NaCl solution, dried over MgSO4 and concentrated to dryness.

Workup

customhas been brought to −78° C.
temperaturethe whole is maintained at that temperature for 1 hour 30 minutes
customis at room temperature
extractionit is extracted with AcOEt
washwashed with a saturated NaCl solution
dry with materialdried over MgSO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-f4dba20fb88e4088bac17bc912ac23d0
Source dataset: uspto-grants-2003_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06638962B2

Reaction notes

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