Tetrahydrofuran → HCID 58409925, compound

HRID 1844906Notes

Reaction equation

HRID 1844906 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH2:16][C:15]=2[C:14]([C:24]#[N:25])=[C:13]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:12]=1.[H-].[Na+].C1C[O:37]CC1>>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:16](=[O:37])[C:15]=2[C:14]([C:24]#[N:25])=[C:13]([N:26]2[CH2:31][CH2:30][CH2:29][CH2:28][CH2:27]2)[CH:12]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409919HCID 58409919, compound

Product 1

HCID 58409925HCID 58409925, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-(naphthalen-2-yl)-2-(piperidin-1-yl)-9H-fluorene-1-carbonitrile (400 mg) in THF was added sodium hydride (32 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 182-184° C.; ESIMS 415 (M++1); IR (KBr) 2213 (CN), 1695 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. additionby dilute HCL
  5. customThe precipitate thus obtained
  6. filtrationwas filtered
  7. custompurified on a silica gel column

Sources & evidence

ORD record
ord-59d70f2d729249828aaa3d2308484666
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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