Diethyl Ether → HCID 88289706, compound

HRID 1720130Notes

Reaction equation

HRID 1720130 reaction equation
[H-].[Na+].C([C:11]([C:16]#[N:17])([CH3:15])[C:12]([O-:14])=[O:13])C[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[C:18]1([Se:24]Br)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C([O-])(O)=O.[Na+].[CH3:31][CH2:32]OCC>C1COCC1>[C:18]1([Se:24][C:10]2[CH:5]=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:16]([CH:11]([CH3:15])[C:12]([O:14][CH:31]([CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:18])[CH3:32])=[O:13])#[N:17]

Participants

7

Reactant 5

HCID 3283Diethyl EtherHCID 24758Sodium hydrideHCID 123446BromoselenobenzeneHCID 516892Sodium BicarbonateHCID 22420428HCID 22420428, compound

Product 1

HCID 88289706HCID 88289706, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a 4-neck 500 ml flask, equipped with a condenser, mechanical stirrer, thermometer, and nitrogen inlet, was added sodium hydride (3.9 g, 153 mmol) and THF (250 ml) under nitrogen. 2-octyl-2-cyanopropionate (20 g, 115 mmol) was added over 10 min. and the reaction mixture was stirred for 1 hour at room temperature. A solution of phenylselenium bromide, prepared by the above method, was added by syringe. The reaction mixture was stirred for 1 hour and added to 250 ml each of ether and sat. aq. NaHCO3. The organic layer was washed twice with 250 ml of H2O and once with 250 ml sat. aq. NaCl. The organic layer was separated, dried (MgSO4) and filtered. Solvent was removed under reduced pressure. Yield=43.2 g (quant.); NMR δ (CDCl3) 7.75 (d, 2H), 7.40 (m, 3H), 4.85 (m, 2H), 1.80 (s, 3H), 0.8-1.70 (m, 16H); IR (neat) 2333, 1734, 1251 cm-1.

Workup

  1. customTo a 4-neck 500 ml flask, equipped with a condenser, mechanical stirrer
  2. additionwas added by syringe
  3. stirringThe reaction mixture was stirred for 1 hour
  4. washThe organic layer was washed twice with 250 ml of H2O and once with 250 ml sat. aq. NaCl
  5. customThe organic layer was separated
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-b3cb761a72c348c3856da12d493893b8
Source dataset
uspto-grants-1996_04
Patent number
US05504252

Reaction notes

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