1,4-Dioxane → 4-[2-(4-Oxido-4-phenyl-1,4-azaphosphinan-1-yl)ethyl]benzoicacid

HRID 1013507Notes

Reaction equation

HRID 1013507 reaction equation
[O:1]=[P:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:7][CH2:6][N:5]([CH2:8][CH2:9][C:10]2[CH:22]=[CH:21][C:13]([C:14]([O:16]C(C)(C)C)=[O:15])=[CH:12][CH:11]=2)[CH2:4][CH2:3]1.O1CCOCC1>Cl>[O:1]=[P:2]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH2:3][CH2:4][N:5]([CH2:8][CH2:9][C:10]2[CH:22]=[CH:21][C:13]([C:14]([OH:16])=[O:15])=[CH:12][CH:11]=2)[CH2:6][CH2:7]1

Participants

4

Reactant 2

HCID 312751,4-DioxaneHCID 57926002tert-Butyl 4-[2-(4-oxido-4-phenyl-1,4-azaphosphinan-1-yl)ethyl]benzoate

Product 1

HCID 579258254-[2-(4-Oxido-4-phenyl-1,4-azaphosphinan-1-yl)ethyl]benzoicacid

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

tert-Butyl 4-[2-(4-oxido-4-phenyl-1,4-azaphosphinan-1-yl)ethyl]benzoate (215 mg, 0.538 mmol) was taken up in 4.0 M HCl in 1,4-dioxane (8.0 mL, 32.0 mmol) and stirred at room temperature overnight. The white slurry was concentrated to dryness, resuspended in MeOH, and concentrated again to afford the title compound as a colorless solid. MS: cal'd 344 (MH+), exp 344 (MH+).

Workup

  1. concentrationThe white slurry was concentrated to dryness
  2. concentrationconcentrated again

Sources & evidence

ORD record
ord-91e942b5540148748a587203a4d49df6
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

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