Sodium hydride → 4-(4-(2-Quinolinylmethyloxy)styryl)benzonitrile

HRID 2073882Notes

Reaction equation

[Cl-].[C:2]([C:4]1[CH:29]=[CH:28][C:7]([CH2:8][P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=[CH:6][CH:5]=1)#[N:3].[H-].[Na+].[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[CH2:42][O:43][C:44]1[CH:51]=[CH:50][C:47]([CH:48]=O)=[CH:46][CH:45]=1>CN(C=O)C>[N:32]1[C:41]2[C:36](=[CH:37][CH:38]=[CH:39][CH:40]=2)[CH:35]=[CH:34][C:33]=1[CH2:42][O:43][C:44]1[CH:45]=[CH:46][C:47]([CH:48]=[CH:8][C:7]2[CH:6]=[CH:5][C:4]([C:2]#[N:3])=[CH:29][CH:28]=2)=[CH:50][CH:51]=1

Participants

Conditions

Temperature: 0 °C

Procedure

A suspension of 5.51 g (13.29 mmol) of (4-cyanobenzyl)triphenylphosphonium chloride in 100 ml of dry DMF under positive nitrogen atmosphere is cooled to 0° C. and 0.50 g (20.77 mmol), of an 80% NaH in oil dispersion is added in small portions. The suspension is aged for 15 minutes at 0° C. followed by 45 minutes at room temperature to assure complete anion formation. The flask is cooled back to 0° C. and 3.5 g (13.29 mmol) of 4-(2-quinolinylmethyloxy)benzaldehyde in 20 ml of DMF is dropped in over a period of 15 minutes. The reaction is allowed to equilibrate to room temperature and stirred for 2 hours. The resultant mixture is poured into ice water and filtered. The precipitate is dissolved in CH2Cl2, dried, and concentrated in vacuo. The crude product is recrystallized from ether to give 4-(4-(2-quinolinylmethyloxy)styryl)benzonitrile. (M.P. 116° C. -118° C.)

Workup

waitfollowed by 45 minutes at room temperature
temperatureThe flask is cooled back to 0° C.
customto equilibrate to room temperature
filtrationfiltered
dissolutionThe precipitate is dissolved in CH2Cl2
customdried
concentrationconcentrated in vacuo
customThe crude product is recrystallized from ether

Sources & evidence

ORD record: ord-3968b315a1444c6c9c5dfbf90e394eca
Source dataset: uspto-grants-1990_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04920133

Reaction notes

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