Trifluoroacetic acid → HCID 17862551, compound

HRID 1766871Notes

Reaction equation

HRID 1766871 reaction equation
[CH2:1]([O:4][P:5]([O:11][CH2:12][C:13]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][C:14]=1[C:15]([O:17]CC1C=CC(OC)=CC=1)=[O:16])([O:7][CH2:8][CH:9]=[CH2:10])=[O:6])[CH:2]=[CH2:3].C1(OC)C=CC=CC=1.FC(F)(F)C(O)=O>C1(C)C=CC=CC=1>[CH2:8]([O:7][P:5]([O:11][CH2:12][C:13]1[CH:30]=[C:29]([C:31]#[N:32])[CH:28]=[CH:27][C:14]=1[C:15]([OH:17])=[O:16])([O:4][CH2:1][CH:2]=[CH2:3])=[O:6])[CH:9]=[CH2:10]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 17862545HCID 17862545, compound

Product 1

HCID 17862551HCID 17862551, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 4-methoxybenzyl 2-[[bis(allyloxy)phosphoryl]oxymethyl]-4-cyanobenzoate (949.1 mg, 2.07 mmol) obtained from Example 4-(5) and anisole (1.0 g, 9.2 mmol) was cooled to 0° C., and trifluoroacetic acid (5 ml) was added thereto. The resulting mixture was warmed to room temperature and allowed to stand for 15 minutes, diluted with toluene, and concentrated under reduced pressure to eliminate the volatile components (repeated three times). Hexane was added to the residue, and then the supernatant solution was removed to give crude 2-[[bis(allyloxy)phosphoryl]oxymethyl]-4-cyanobenzoic acid. This crude product was dissolved in dichloromethane (20 ml), and oxalyl chloride (1.27 g, 10 mmol) and N,N-dimethylformamide (15 μl) were added thereto at 0° C. The mixture was warmed to room temperature and stirred for 30 minutes, and the solvent was distilled off under reduced pressure. The residue was diluted with toluene, and the solution was concentrated under reduced pressure to eliminate the volatile components (repeated three times), and crude 2-[[bis(allyloxy)phosphoryl]oxymethyl]-4-cyanobenzoyl chloride was obtained.

Workup

  1. concentrationconcentrated under reduced pressure
  2. additionHexane was added to the residue
  3. customthe supernatant solution was removed

Sources & evidence

ORD record
ord-a2e208c0bb31430db4394fd4ec3036d8
Source dataset
uspto-grants-2007_06
Patent number
US07230023B2

Reaction notes

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