2-[3-Cyano-4,5,5-trimethylfuran-2(5H)-ylidene]malononitrile → 2-[4-[2-[2-(tert-butyldiphenylsiloxy)-4-dibutylaminophenyl]vinyl]-3-cyano-5,5-dimethyl-2(5H)-furanylidene]propanedinitrile

HRID 85319Notes

Reaction equation

[O:1]([C:19]1[CH:26]=[C:25]([N:27]([CH2:32][CH2:33][CH2:34][CH3:35])[CH2:28][CH2:29][CH2:30][CH3:31])[CH:24]=[CH:23][C:20]=1[CH:21]=O)[Si:2]([C:15]([CH3:18])([CH3:17])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[C:36]([C:38]1[C:39](=[C:46]([C:49]#[N:50])[C:47]#[N:48])[O:40][C:41]([CH3:45])([CH3:44])[C:42]=1[CH3:43])#[N:37]>C(O)C>[O:1]([C:19]1[CH:26]=[C:25]([N:27]([CH2:28][CH2:29][CH2:30][CH3:31])[CH2:32][CH2:33][CH2:34][CH3:35])[CH:24]=[CH:23][C:20]=1[CH:21]=[CH:43][C:42]1[C:41]([CH3:44])([CH3:45])[O:40][C:39](=[C:46]([C:47]#[N:48])[C:49]#[N:50])[C:38]=1[C:36]#[N:37])[Si:2]([C:15]([CH3:17])([CH3:18])[CH3:16])([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In 5 ml of ethanol were dissolved 200 mg (0.41 mmol) of 2-(tert-butyldiphenylsiloxy)-4-dibutylaminobenzaldehyde and mg (0.45 mmol) of 2-(3-cyano-4,5,5-trimethyl-2(5H)-furanylidene)propanedinitrile. After the mixture was stirred with heating at 60° C. for 3 hours, the precipitate was separated by filtration and washed with methanol. The crystal was purified by silica gel column chromatography and washed with methanol to give 199 mg of a dark brown crystal having a mp of 220-221° C. (yield: 72.6%).

Workup

customthe precipitate was separated by filtration
washwashed with methanol
customThe crystal was purified by silica gel column chromatography
washwashed with methanol

Sources & evidence

ORD record: ord-e6a3d15e954d45108a54c8791bff0078
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846955B2

Reaction notes

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