Tetrahydrofuran → HCID 58409944, compound

HRID 1844910Notes

Reaction equation

HRID 1844910 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[CH2:13][C:12]=3[C:11]([C:21]#[N:22])=[C:10]([N:23]3[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24]3)[CH:9]=2)=[CH:4][CH:3]=1.[H-].[Na+].C1C[O:34]CC1>>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:20]3[C:19]4[C:14](=[CH:15][CH:16]=[CH:17][CH:18]=4)[C:13](=[O:34])[C:12]=3[C:11]([C:21]#[N:22])=[C:10]([N:23]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28]3)[CH:9]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409908HCID 58409908, compound

Product 1

HCID 58409944HCID 58409944, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-(4-fluorophenyl)-2-(piperidin-1-yl)-9H-fluorene-1-carbonitrile (368 mg) in THF was added sodium hydride (38 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 152-154° C.; ESIMS 383 (M++1); IR (KBr) 1708 cm−1 (CO), 2221 (CN); HRMS calcd. for C25H19 FN2O 382.1481 found 382.1471.

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-c7313296a4b0464f856e294027e129bf
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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