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

HRID 522877ノート

反応式

HRID 522877 の反応式
[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

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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%

出典と根拠

ORDレコード
ord-c31e993c8b884d888ca467cb33b4e20b
出典データセット
uspto-grants-2016_05
特許番号
US09334269B2

反応ノート

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