Tetrahydrofuran → HCID 58409934, compound

HRID 1844903Notes

Reaction equation

HRID 1844903 reaction equation
[C:1]1([C:7]2[C:19]3[C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[CH2:12][C:11]=3[C:10]([C:20]#[N:21])=[C:9]([N:22]3[CH2:26][CH2:25][CH2:24][CH2:23]3)[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].C1C[O:32]CC1>>[O:32]=[C:12]1[C:11]2[C:10]([C:20]#[N:21])=[C:9]([N:22]3[CH2:23][CH2:24][CH2:25][CH2:26]3)[CH:8]=[C:7]([C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:19]=2[C:18]2[C:13]1=[CH:14][CH:15]=[CH:16][CH:17]=2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 58409935HCID 58409935, compound

Product 1

HCID 58409934HCID 58409934, compound

Conditions

Temperature
2.5 °C

Procedure

A solution of 4-phenyl-2-(pyrrolidin-1-yl)-9H-fluorene-1-carbonitrile (336 mg) in THF was added sodium hydride (25 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 166-168° C.; ESIMS 351 (M++1); IR (KBr) 2215 (CN), 1717 cm−1 (CO); 1H NMR (300 Hz, CDCl3) δ 1.97-2.10 (m, 4H, CH2), 3.67-3.73 (m, 4H, 2CH2), 6.43-6.48 (m, 1H, ArH), 6.59 (s, 1H, ArH), 7.04-7.12 (m, 2H, ArH), 7.40-7.47 (m, 2H, ArH), 7.48-7.54 (m, 3H, ArH), 7.55-7.59 (m, 1H, ArH); 13C NMR (75.53 MHz, CDCl3): δ 24.50, 49.37, 88.60, 115.58, 11927, 120.14, 123.11, 126.0, 127.12, 127.33, 127.49, 129.34, 132.13, 133.40, 136.26, 137.69, 141.23, 142.34, 149.32, 189.94.

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-8ed9fabe36d445a780eb1d56c744fbec
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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