Acetonitrile → HCID 178455791, compound

HRID 1364303Notes

Reaction equation

HRID 1364303 reaction equation
[C:1]([O-:4])([O-])=[O:2].[K+].[K+].[C:7]1([CH3:19])[CH:12]=CC(S(N=[N+]=[N-])(=O)=O)=[CH:9][CH:8]=1.O=[C:21]([CH3:29])[CH2:22]P(=O)(OC)OC.[CH3:30]C#N>CO>[CH3:30][O:4][C:1]([C@H:21]1[CH2:29][CH2:19][C@H:7]([C:8]#[CH:9])[CH2:12][CH2:22]1)=[O:2]

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 11430Potassium CarbonateHCID 13661p-Toluenesulfonyl azideHCID 77872Dimethyl (2-oxopropyl)phosphonate

Product 1

HCID 178455791HCID 178455791, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

K2CO3 (3.4 g, 24.7 mmol) was added to a solution of p-toluenesulfonyl azide (1.97 g, 9.9 mmol) and dimethyl (2-oxo-propyl)phosphonate (1.73 g, 9.9 mmol) in MeCN (110 mL) at rt. The mixture was stirred at rt for 2 h before addition of a solution of intermediate 5.iii (1.2 g, 7 mmol) in MeOH (15.5 mL). The mixture was stirred at rt overnight, concentrated in vacuo and partitioned between DCM and water. The organic phase was dried over MgSO4 and concentrated. The residue was purified by chromatography over SiO2 (Hex/EA 4:1) to give the title alkyne (0.45 g, 38% yield) as a colourless oil.

Workup

  1. concentrationconcentrated in vacuo
  2. custompartitioned between DCM and water
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by chromatography over SiO2 (Hex/EA 4:1)

Sources & evidence

ORD record
ord-df9cf6cb66274aa9b9fe8f4d6dce2284
Source dataset
uspto-grants-2011_02
Patent number
US07888359B2

Reaction notes

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