Tetrahydrofuran → HCID 58409930, compound

HRID 1844908Notes

Reaction equation

HRID 1844908 reaction equation
[N:1]1([C:7]2[CH:19]=[C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=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:25]#[N:26])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].C1C[O:32]CC1>>[O:32]=[C:10]1[C:9]2[C:8]([C:25]#[N:26])=[C:7]([N:1]3[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]3)[CH:19]=[C:18]([C:20]3[S:21][CH:22]=[CH:23][CH:24]=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 58409912HCID 58409912, compound

Product 1

HCID 58409930HCID 58409930, compoundYield 73%

Conditions

Temperature
2.5 °C

Procedure

A solution of 2-(piperidin-1-yl)-4-(thiophen-2-yl)-9H-fluorene-1-carbonitrile (356 mg) in THF was added sodium hydride (29 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 73%; mp 226-228° C.; ESMS 371 (M++1); IR (KBr) 1710 cm−1 (CO), 2220 (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-9f4cad08719644179d600c5b21ada059
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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