Tetrahydrofuran → HCID 66884299, compound

HRID 1844909Notes

Reaction equation

HRID 1844909 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH2:14][C:13]=3[C:12]([C:22]#[N:23])=[C:11]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:10]=2)=[CH:5][CH:4]=1.[H-].[Na+].C1C[O:35]CC1>>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]2[C:21]3[C:20]4[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=4)[C:14](=[O:35])[C:13]=3[C:12]([C:22]#[N:23])=[C:11]([N:24]3[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]3)[CH:10]=2)=[CH:7][CH:8]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409937HCID 58409937, compound

Product 1

HCID 66884299HCID 66884299, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-(4-methoxyphenyl)-2-(piperidin-1-yl)-9H-fluorene-1-carbonitrile (380 mg) in THF was added sodium hydride (33 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. Red solid; mp 210-212° C.;. FAB MS 395 (M+); IR (KBr) 2210 (CN), 1703 cm−1 (CO); HRMS calcd. for C26H22N2O2 394.1681 found 394, 1689.

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-bf8de62034b140d18854bb58c0592d81
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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