Water → HCID 20509326, compound

HRID 1758476Notes

Reaction equation

HRID 1758476 reaction equation
[H-].[Na+].P(=O)([O-])O[C:5](CC)(CC)[C:6]#[N:7].[C:14]([O:18][C:19](=[O:28])[NH:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH:26]=O)([CH3:17])([CH3:16])[CH3:15].O>COCCOC>[C:14]([O:18][C:19](=[O:28])[NH:20][CH:21]([CH2:5][C:6]#[N:7])[CH2:22][CH2:23][CH2:24][CH:25]=[CH2:26])([CH3:17])([CH3:16])[CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 10536636tert-Butyl 6-oxohexylcarbamateHCID 178449162HCID 178449162, compound

Product 1

HCID 20509326HCID 20509326, compound

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
20 °C

Procedure

Sodium hydride (50% suspension in oil, 1.2 g, 0.025 mol) is placed in 100 ml of dry 1.2-dimethoxyethane. The slurry is cooled to 20° C. and diethylcyanomethyl phosphonate (4.43 g, 0.025 mol) is added dropwise with stirring. After the addition, the solution is stirred at room temperature for 1 hour until gas evolution has ceased. To the yellow solution, maintained below 25° C., is added dropwise t-butyl(5-formylpentyl)carbamate (5.38 g, 0.025 mol). The solution is stirred at room temperature for 1 hour and refluxed for 0.5 hour. A large excess of water is added and the product t-butyl-(7-cyanohepten-6-yl)carbamate (3.63 g, 61%) is extracted with ether.

Workup

  1. additionAfter the addition
  2. stirringthe solution is stirred at room temperature for 1 hour until gas evolution
  3. temperatureTo the yellow solution, maintained below 25° C.
  4. stirringThe solution is stirred at room temperature for 1 hour
  5. temperaturerefluxed for 0.5 hour
  6. extractionthe product t-butyl-(7-cyanohepten-6-yl)carbamate (3.63 g, 61%) is extracted with ether

Sources & evidence

ORD record
ord-2ca1487f2f4343429a5c5168416505c4
Source dataset
uspto-grants-1983_02
Patent number
US04374128

Reaction notes

Loading…