Tetrahydrofuran → HCID 18425700, compound

HRID 1280773Notes

Reaction equation

HRID 1280773 reaction equation
[H-].[Na+].C1COCC1.C(OP([CH2:16][C:17]#[N:18])(=O)OCC)C.[C:19]1([CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:26]2[CH2:31][CH2:30][C:29](=O)[CH2:28][CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>O.C(OC(=O)C)C>[C:19]1([CH:25]([C:33]2[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=2)[N:26]2[CH2:31][CH2:30][C:29](=[CH:16][C:17]#[N:18])[CH2:28][CH2:27]2)[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 8028Tetrahydrofuran3×HCID 24758Sodium hydrideHCID 75676Diethyl (cyanomethyl)phosphonateHCID 15541260HCID 15541260, compound

Product 1

HCID 18425700HCID 18425700, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

2.9 g (97 mmol) 80% sodium hydride are suspended in abs. THF and a solution of 21.5 g (121 mmol) diethyl-(cyanomethyl)-phosphonate in 150 ml abs. THF is added dropwise under light cooling. The mixture is subsequently stirred 30 minutes at RT and then a solution of 26.5 g (100 mmol) N-(diphenylmethyl)4-piperidone in 80 ml abs. THF is added dropwise. The suspension is left to stand overnight and subsequently added to 200 ml acetic acid ethyl ester and 100 ml water. The organic phase is separated and washed with 100 ml water, dried over sodium sulfate and the solvent is removed under vacuum. The residue is chromatographically purified over silica gel with dichloromethane. Yield: 22.7 g (78%).

Workup

  1. temperaturecooling
  2. waitThe suspension is left
  3. waitto stand overnight
  4. customThe organic phase is separated
  5. washwashed with 100 ml water
  6. dry with materialdried over sodium sulfate
  7. customthe solvent is removed under vacuum
  8. customThe residue is chromatographically purified over silica gel with dichloromethane

Sources & evidence

ORD record
ord-e69d14cce28e4d8583a86fc45be6eb57
Source dataset
uspto-grants-2002_09
Patent number
US06451816B1

Reaction notes

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