Hydrochloric Acid → HCID 86652435, compound

HRID 2358916Notes

Reaction equation

[C:1]1([Si:7]([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)([C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:8]2[CH:39]=[CH:38][C:11]3[O:12][C:13]4[CH:18]=[CH:17][C:16]([Si:19]([C:32]5[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=5)([C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[C:20]5[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=5)=[CH:15][C:14]=4[C:10]=3[CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.CN([CH:55]=[O:56])C.Cl>C1COCC1.C1CCCCC1>[C:32]1([Si:19]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:16]2[CH:17]=[C:18]([CH:55]=[O:56])[C:13]3[O:12][C:11]4[CH:38]=[CH:39][C:8]([Si:7]([C:1]5[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=5)([C:40]5[CH:41]=[CH:42][CH:43]=[CH:44][CH:45]=5)[C:46]5[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=5)=[CH:9][C:10]=4[C:14]=3[CH:15]=2)[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=1

Participants

Conditions

Temperature: 45 °C

Procedure

1 g (1.46 mmol) 2,8-di-(triphenylsilyl)-dibenzofuran are dissolved in 100 ml dry THF at 45° C. and 10 ml of 1.4 M sec-Buthyllithium solution in cyclohexane is added. After stirring for 15 min. at 45° C., 2 ml of dry DMF is added; the reaction mixture is stirred for 1 h. 100 ml of 0.5 M HCl is added to quench the reaction. The product is extracted with ethylacetate and purified by column chromatography on silica gel with heptane:ethylacetate (3:1) as an eluent. 2,8-di-(triphenylsilyl)-dibenzofuran-4-carboxaldehyde (5.3) is obtained in 30.2% yield.

Workup

stirringthe reaction mixture is stirred for 1 h
customto quench
customthe reaction
extractionThe product is extracted with ethylacetate
custompurified by column chromatography on silica gel with heptane:ethylacetate (3:1) as an eluent

Sources & evidence

ORD record: ord-8b7ad890decf4837b63a30d7eb78c575
Source dataset: uspto-grants-2014_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08685541B2

Reaction notes

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