Tetrahydrofuran → HCID 58409914, compound

HRID 1844912Notes

Reaction equation

HRID 1844912 reaction equation
[N:1]1([C:6]2[CH:18]=[C:17]([C:19]3[CH:24]=[CH:23][C:22]([CH3:25])=[CH:21][CH:20]=3)[C:16]3[C:15]4[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=4)[CH2:9][C:8]=3[C:7]=2[C:26]#[N:27])[CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1C[O:33]CC1>>[O:33]=[C:9]1[C:8]2[C:7]([C:26]#[N:27])=[C:6]([N:1]3[CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:18]=[C:17]([C:19]3[CH:20]=[CH:21][C:22]([CH3:25])=[CH:23][CH:24]=3)[C:16]=2[C:15]2[C:10]1=[CH:11][CH:12]=[CH:13][CH:14]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409954HCID 58409954, compound

Product 1

HCID 58409914HCID 58409914, compoundYield 76%

Conditions

Temperature
2.5 °C

Procedure

A solution of 2-(pyrrolidin-1-yl)-4-p-tolyl-9H-fluorene-1-carbonitrile (350 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. Red solid; yield 76%; mp 162-164° C.; ESMS 365 (M++1); IR (KBr) 1716 cm−1 (CO) 2214 (CN).

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-5aa8f16b97d14ca4ad16372ba350cd24
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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