Tetrahydrofuran → HCID 58409929, compound

HRID 1844907Notes

Reaction equation

HRID 1844907 reaction equation
[N:1]1([C:7]2[CH:19]=[C:18]([C:20]3[C:33]4[C:34]5=[C:35]6[C:30](=[CH:31][CH:32]=4)[CH:29]=[CH:28][CH:27]=[C:26]6[CH:25]=[CH:24][C:23]5=[CH:22][CH:21]=3)[C:17]3[C:16]4[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=4)[CH2:10][C:9]=3[C:8]=2[C:36]#[N:37])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1C[O:43]CC1>>[O:43]=[C:10]1[C:9]2[C:8]([C:36]#[N:37])=[C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:19]=[C:18]([C:20]3[C:33]4[C:34]5=[C:35]6[C:30](=[CH:31][CH:32]=4)[CH:29]=[CH:28][CH:27]=[C:26]6[CH:25]=[CH:24][C:23]5=[CH:22][CH:21]=3)[C:17]=2[C:16]2[C:11]1=[CH:12][CH:13]=[CH:14][CH:15]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409948HCID 58409948, compound

Product 1

HCID 58409929HCID 58409929, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 2-(piperidin-1-yl)-4-(pyren-1-yl)-9H-fluorene-1-carbonitrile (474 mg) in THF was added sodium hydride (42 mg) and was stirred at 0-5° C. for less than five minutes. After completion, the reaction solvent was evaporated under vacuum and the crude solid obtained was quenched with ice water and subsequently neutralized by dilute HCl. The precipitate thus obtained was filtered and purified on a silica gel column using ethyl acetate-hexane as eluent. Light red solid; mp 180-182° C.; ESMS 489 (M+1); IR (KBr) 2217 (CN), 1713 cm−1 (CO).

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum
  2. customthe crude solid obtained
  3. customwas quenched with ice water
  4. customThe precipitate thus obtained
  5. filtrationwas filtered
  6. custompurified on a silica gel column

Sources & evidence

ORD record
ord-2cbd33651d1846b2bffd63b0cafc2300
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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