Sodium hydride → HCID 58409921, compound

HRID 1844894Notes

Reaction equation

HRID 1844894 reaction equation
O=[C:2]1O[C:6]2[C:8]3[C:13]([CH2:14][C:5]=2[C:4]([N:15]2[CH2:19][CH2:18][CH2:17][CH2:16]2)=[C:3]1[C:20]#[N:21])=[CH:12][CH:11]=[CH:10][CH:9]=3.[H-].[Na+]>C1COCC1>[N:15]1([C:4]2[C:3]([C:20]#[N:21])=[C:2]3[C:5]([CH2:6][C:8]4[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=43)=[C:6]3[C:8]4[C:13]([CH2:14][C:5]=23)=[CH:12][CH:11]=[CH:10][CH:9]=4)[CH2:19][CH2:18][CH2:17][CH2:16]1

Participants

4

Reactant 2

HCID 24758Sodium hydrideHCID 67394160HCID 67394160, compound

Product 1

HCID 58409921HCID 58409921, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2-oxo-4-(pyrrolidin-1-yl)-2,5-dihydroindeno[1,2-b]pyran-3-carbonitrile (278 mg), indanone-1 (132 mg) and NaH (46 mg) in THF was stirred for <5 min. After completion, the reaction solvent was evaporated under vacuum to dryness and crude solid was quenched with ice water and subsequently neutralized with dil. HCl, finally purified by column chromatography using ethylacetate-hexane as eluent. White solid; mp 158-160° C.; 1H NMR (300 MHz, CDC3) δ 2.01-2.10 (m, 2H, CH2), 3.75-3.85 (m, 4H, 2CH2), 4.12-4.15 (m, 4H, 2CH2), 7.38-7.50 (m, 4H, ArH), 7.58-7.67 (m, 2H, ArH), 7.95 (d, J=7.3 Hz, 1H, ArH), 8.62 (d, J=7.5 Hz, 1H, ArH); IR (KBr) 2199 cm−1 (CN); MS (ESI) 349 (M++1).

Workup

  1. customAfter completion, the reaction solvent was evaporated under vacuum to dryness
  2. customcrude solid was quenched with ice water
  3. customfinally purified by column chromatography

Sources & evidence

ORD record
ord-162fb298c4d2461d9efab54d7d4a85a8
Source dataset
uspto-grants-2015_02
Patent number
US08946682B2

Reaction notes

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