Cyanomethylenetributylphosphorane → HCID 66861351, compound

HRID 253006Notes

Reaction equation

HRID 253006 reaction equation
C(C=P(CCCC)(CCCC)CCCC)#N.O[CH2:18][C@@H:19]([N:22]([CH2:35][CH2:36][OH:37])[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])(=[O:25])=[O:24])[CH2:20][CH3:21]>C1(C)C=CC=CC=1>[CH2:20]([C@H:19]1[CH2:18][O:37][CH2:36][CH2:35][N:22]1[S:23]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=1[N+:32]([O-:34])=[O:33])(=[O:24])=[O:25])[CH3:21]

Participants

4

Reactant 2

HCID 4622928CyanomethylenetributylphosphoraneHCID 66861453HCID 66861453, compound

Product 1

HCID 66861351HCID 66861351, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A 1 M solution of 0.558 ml (0.558 mmol) of (cyanomethylene)tributylphosphorane in toluene was added to a solution of 95 mg (0.298 mmol) of the title compound produced in step (ii) of Reference Example 9 in toluene (3 ml), and the mixture was stirred with heating under reflux for 1 hr 20 min. Thereafter, the reaction solution was cooled to room temperature, and the solvent was removed under the reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:4) to give 89 mg (yield 99%) of the title compound.

Workup

  1. temperaturewith heating
  2. temperatureunder reflux for 1 hr 20 min
  3. customthe solvent was removed under the reduced pressure
  4. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:4)

Sources & evidence

ORD record
ord-a043bcd51ebd484a8187116f04ef9781
Source dataset
uspto-grants-2011_01
Patent number
US07871982B2

Reaction notes

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