Decylamine → HCID 66761196, compound

HRID 561807Notes

Reaction equation

HRID 561807 reaction equation
[C:1]([CH2:3]P(=O)(OCC)OCC)#[N:2].CC(C)([O-])C.[K+].[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[Cl:35])[CH:30]=O)([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19].CCCCCCCCCCN>C1COCC1>[Si:18]([O:25][CH2:26][C:27]1[CH:28]=[C:29](/[CH:30]=[CH:3]/[C:1]#[N:2])[CH:32]=[CH:33][C:34]=1[Cl:35])([C:21]([CH3:24])([CH3:23])[CH3:22])([CH3:20])[CH3:19]

Participants

6

Reactant 4

HCID 8916DecylamineHCID 75676Diethyl (cyanomethyl)phosphonateHCID 23665647Potassium tert-butoxideHCID 86635911HCID 86635911, compound

Product 1

HCID 66761196HCID 66761196, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of diethyl cyanomethylphosphonate (1.1 eq.) in THF (0.14 M) was added at 0° C. potassium tert-butoxide (1 M THF solution, 1.1 eq.). The resulting yellow solution was stirred at 0° C. for 1 h before 3-({[tert-butyl(dimethyl)silyl]oxy}methyl)-4-chlorobenzaldehyde from step 3 of Amine 10 synthesis (1 eq.) in THF (0.14 M) was added. The resulting mixture was stirred at RT 3 h. The reaction was quenched by the addition of sat. aq. NH4Cl and then extracted with EtOAc. The combined organic extracts were washed with sat. aq. NaHCO3, dried over MgSO4 and filtered. Concentration of the filtrate in vacuo afforded an orange oil. Purification of the crude product thus obtained by way of flash chromatography (SiO2, Hex→2:1 (v/v) Hex:EtOAc) afforded the title compound.

Workup

  1. additionwas added
  2. customThe reaction was quenched by the addition of sat. aq. NH4Cl
  3. extractionextracted with EtOAc
  4. washThe combined organic extracts were washed with sat. aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customConcentration of the filtrate in vacuo afforded an orange oil
  8. customPurification of the crude product
  9. customthus obtained by way of flash chromatography (SiO2, Hex→2:1 (v/v) Hex:EtOAc)

Sources & evidence

ORD record
ord-7976e5bc5bd24c039b8e7529d4b90319
Source dataset
uspto-grants-2011_11
Patent number
US08063105B2

Reaction notes

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