Sodium hydride → HCID 59600214, compound

HRID 2267720Notes

Reaction equation

HRID 2267720 reaction equation
[H-].[Na+].[NH:3]1[C:8](=O)[CH2:7][O:6][CH2:5][C:4]1=[O:10].F[B-](F)(F)F.[C:16]([C:21]1([P+](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[CH2:23][CH2:22]1)([O:18][CH2:19][CH3:20])=[O:17]>C1COCC1>[CH2:19]([O:18][C:16]([C:21]1[CH2:22][CH2:23][N:3]2[C:4](=[O:10])[CH2:5][O:6][CH2:7][C:8]=12)=[O:17])[CH3:20]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 364836Morpholine-3,5-dioneHCID 11016017(1-(Ethoxycarbonyl)cyclopropyl)triphenylphosphonium tetrafluoroborate

Product 1

HCID 59600214HCID 59600214, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a suspension of sodium hydride (480 mg, 60% in mineral oil, 12 mmol) in 10 ml of anhydrous THF is added morpholine-3,5-dione (1.2 g, 10 mmol) in 20 ml of THF under an argon athmosphere. After 10 min., 1-carbethoxycyclopropyltriphenylphosphonium tetrafluoroborate (Fuchs' reagent, 6.8 g, 11 mmol)) in 20 ml of THF are added and the mixture is refluxed for 21 hours. After cooling, the suspension is concentrated on a rotary evaporator, poured onto ice/sat. sodium bicarbonate solution, and extracted three times with ether. The combined organic phases are washed with brine, dried over anhydrous sodium sulphate, and evaporated. The residual yellow oil (3.04 g) is purified by chromatography (Silica gel 60, 0.063-0.2 mesh, cyclohexane/ethyl acetate 1:1).

Workup

  1. temperaturethe mixture is refluxed for 21 hours
  2. temperatureAfter cooling
  3. concentrationthe suspension is concentrated on a rotary evaporator
  4. additionpoured onto ice/
  5. extractionsodium bicarbonate solution, and extracted three times with ether
  6. washThe combined organic phases are washed with brine
  7. dry with materialdried over anhydrous sodium sulphate
  8. customevaporated
  9. customThe residual yellow oil (3.04 g) is purified by chromatography (Silica gel 60, 0.063-0.2 mesh, cyclohexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-a1d6696ad68e48e6b3ea797a6bde3abf
Source dataset
uspto-grants-2010_12
Patent number
US07858781B2

Reaction notes

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