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

HRID 1013506
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HRID 1013506 반응식
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
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6342Acetonitrile용매
HCID 8857
Ethyl Acetate
용매

실험 절차

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+).

후처리

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

출처 및 근거

ORD 기록
ord-00799fb313094cf28abc007f24e54394
출처 데이터셋
uspto-grants-2011_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07981874B2

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