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

HRID 522877Notes

Reaction equation

HRID 522877 reaction equation
[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

Participants

6

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  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%

Sources & evidence

ORD record
ord-c31e993c8b884d888ca467cb33b4e20b
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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