4-Chlorophenol → Tert-butyl 3-(1-(4-chlorophenoxy)ethyl)-azetidine-1-carboxylate

HRID 522877노트

반응식

HRID 522877 반응식
[OH:1][CH:2]([CH:4]1[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[O:9])[CH2:5]1)[CH3:3].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38](O)=[CH:37][CH:36]=1.CCOC(/N=N/C(OCC)=O)=O>C1COCC1>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([O:1][CH:2]([CH:4]2[CH2:7][N:6]([C:8]([O:10][C:11]([CH3:13])([CH3:12])[CH3:14])=[O:9])[CH2:5]2)[CH3:3])=[CH:37][CH:36]=1

참가 물질

6

반응물 4

HCID 46844-ChlorophenolHCID 11776TriphenylphosphineHCID 5462977Diethyl azodicarboxylateHCID 58348207Tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate

생성물 1

HCID 86685242Tert-butyl 3-(1-(4-chlorophenoxy)ethyl)-azetidine-1-carboxylate수율 44.2%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a flask charged with tert-butyl 3-(1-hydroxyethyl)azetidine-1-carboxylate (212 mg, 1.053 mmol) was added THF (6.3 mL), resin bound PPh3 (527 mg, 1.580 mmol), p-chlorophenol (104 μL, 1.053 mmol) and DEAD (250 μL, 1.580 mmol). The reaction mixture was stirred overnight at RT. The reaction mixture was filtered through cotton and dried under reduced pressure, then purified with flash chromatography ramping CH2Cl2:MeOH:NH4OH (90:10:1) in CH2Cl2 from 0% to 100% to afford tert-butyl 3-(1-(4-chlorophenoxy)ethyl)-azetidine-1-carboxylate (145 mg, 44%) as a yellow oil.

후처리

  1. filtrationThe reaction mixture was filtered through cotton
  2. customdried under reduced pressure
  3. custompurified with flash chromatography ramping CH2Cl2:MeOH:NH4OH (90:10:1) in CH2Cl2 from 0% to 100%

출처 및 근거

ORD 기록
ord-c31e993c8b884d888ca467cb33b4e20b
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09334269B2

반응 노트

불러오는 중…