Potassium Carbonate → tert-Butyl 4-[2-(4-oxido-4-phenyl-1,4-azaphosphinan-1-yl)ethyl]benzoate

HRID 1013506Notes

Reaction equation

HRID 1013506 reaction equation
Cl.[C:2]1([P:8]2(=[O:14])[CH2:13][CH2:12][NH:11][CH2:10][CH2:9]2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:16][CH2:17][C:18]1[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:28])([CH3:27])[CH3:26])=[O:23])=[CH:20][CH:19]=1.C([O-])([O-])=O.[K+].[K+]>CC#N.CCOC(C)=O>[O:14]=[P:8]1([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[CH2:9][CH2:10][N:11]([CH2:16][CH2:17][C:18]2[CH:30]=[CH:29][C:21]([C:22]([O:24][C:25]([CH3:27])([CH3:26])[CH3:28])=[O:23])=[CH:20][CH:19]=2)[CH2:12][CH2:13]1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 10803033Tert-butyl 4-(2-bromoethyl)benzoateHCID 668324724-Phenyl-1,4lambda5-azaphosphinan-4-one hydrochloride

Product 1

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

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-Phenyl-1,4-azaphosphinane 4-oxide hydrochloride (200 mg, 0.863 mmol), tert-butyl 4-(2-bromoethyl)benzoate (246 mg, 0.863 mmol), and K2CO3 (358 mg, 2.59 mmol) were combined in MeCN (10 mL) and stirred at reflux overnight. The reaction was cooled, diluted with EtOAc, washed with water and brine, dried (MgSO4), and evaporated. Flash chromatography (0-10% MeOH/CH2Cl2) afforded the title compound as a colorless solid. 1H NMR (CDCl3, 600 MHz) δ 7.88 (d, J=8.4 Hz, 2H), 7.76-7.71 (m, 2H), 7.54-7.45 (m, 3H), 7.21 (d, J=8.2 Hz, 2H), 3.09-2.99 (m, 4H), 2.85-2.80 (m, 2H), 2.77-2.73 (m, 2H), 2.19-2.11 (m, 2H), 2.08-1.98 (m, 2H), 1.55 (s, 9H). MS: cal'd 400 (MH+), exp 400 (MH+).

Workup

  1. temperatureat reflux overnight
  2. temperatureThe reaction was cooled
  3. washwashed with water and brine
  4. dry with materialdried (MgSO4)
  5. customevaporated

Sources & evidence

ORD record
ord-00799fb313094cf28abc007f24e54394
Source dataset
uspto-grants-2011_07
Patent number
US07981874B2

Reaction notes

Loading…