Sodium hydride → HCID 69205993, compound

HRID 840106Notes

Reaction equation

HRID 840106 reaction equation
[H-].[Na+].[NH:3]1[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[CH:5]=[CH:4]1)[N:12]=[CH:11][CH:10]=[CH:9]3.[CH2:16]1[O:19][C@@H:17]1[CH3:18].[Cl-].[NH4+]>C1COCC1>[N:3]1([CH2:16][C@H:17]([OH:19])[CH3:18])[C:7]2=[C:8]3[C:13](=[CH:14][CH:15]=[C:6]2[CH:5]=[CH:4]1)[N:12]=[CH:11][CH:10]=[CH:9]3

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 146261(R)-1,2-EpoxypropaneHCID 178420737HCID 178420737, compound

Product 1

HCID 69205993HCID 69205993, compoundYield 18.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride, 60% dispersion in mineral oil, (0.76 g, 18.5 mmol) and THF (30 mL) was cooled to 0° C. under Ar. A mixture of 1H-pyrrolo[2,3-f]quinoline (G. Bartoli, G. Palmieri, M. Bosco and R. Dalpozzo, Tetrahedron Letts., 1989, 30, 2129-2132) (2.5 g, 14.8 mmol) and THF (20 mL) was added and the mixture was left at 0° C. for 1 h. (R)-propylene oxide (2.1 mL, 30 mmol) was added and the mixture was left at room temperature for 48 h. Saturated ammonium chloride solution (100 mL) was added and the mixture was extracted with Et2O (3×100 mL), the extracts were combined, washed with brine (2×100 mL), dried (MgSO4), concentrated in vacuo and purified by column chromatography [SiO2; Et2O] to give the product (0.61 g, 18% yield) as a pale yellow oil: IRνmax(Nujol)/cm−1 3106, 1361, 1117, 826, 805, and 731; NMR δH (400 MHz, CDCl3) 1.35 (3H, d, J 6.5 Hz), 2.76 (1H, br), 4.33 (1H, m), 4.44 (1H, m), 4.56 (I1H, m), 6.64 (1H, d, J 3.0 Hz), 7.20 (1H, d, J 3.0 Hz), 7.30 (1H, dd, J8.5 and 4.5 Hz), 7.71 (1H, d, J 9.0 Hz), 7.87 (1H, d, J 9.0 Hz), 8.52 (1H, d, J 8.5 Hz) and 8.67 (1H, m).

Workup

  1. additionwas added
  2. additionwas added
  3. extractionthe mixture was extracted with Et2O (3×100 mL)
  4. washwashed with brine (2×100 mL)
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. custompurified by column chromatography [SiO2; Et2O]

Sources & evidence

ORD record
ord-712b8c72b15e47918245a7bc9d78e18b
Source dataset
uspto-grants-2002_04
Patent number
US06365598B1

Reaction notes

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