4-Nitrophenethyl alcohol → HCID 18765769, compound
Reaction equation
Cl.[C:2]1([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CCN(CC)CC.C(P(CCCC)CCCC)CCC.[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([CH2:41][CH2:42]O)=[CH:39][CH:38]=1)([O-:36])=[O:35].CCOC(/N=N/C(OCC)=O)=O.[NH4+].[Cl-]>C(Cl)Cl>[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([CH2:41][CH2:42][N:11]2[CH2:10][CH:9]=[C:8]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)[CH2:13][CH2:12]2)=[CH:39][CH:38]=1)([O-:36])=[O:35]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 23 °C
Procedure
1.29 g (6.6 mmol) of 4-phenyl-1,2,3,6-tetrahydropyridine hydrochloride, 0.92 ml (6.6 mmol) of Et3N and 1.62 ml (6.6 mmol) of tributylphosphine are added to a solution of 1.0 g (5.98 mmol) of 4-nitrophenethyl alcohol in 25 ml of CH2Cl2. The reaction mixture is agitated vigorously at 23° C. and 1.04 ml (6.6 mmol) of diethylazodicarboxylate is added dropwise. After 4 hours, the reaction is stopped by adding 5 ml of a saturated solution of NH4Cl. After decantation, the aqueous phase is extracted twice with 5 ml of CH2Cl2, the organic phases are combined and washed twice with 5 ml of water, twice with 5 ml of brine, dried over magnesium sulphate, filtered and concentrated under vacuum. The residue is purified on a silica column (eluent Heptane/AcOEt: 9/1 to 7/3) in order to produce 1.20 g of the expected product.
Workup
- extractionAfter decantation, the aqueous phase is extracted twice with 5 ml of CH2Cl2
- washwashed twice with 5 ml of water, twice with 5 ml of brine
- dry with materialdried over magnesium sulphate
- filtrationfiltered
- concentrationconcentrated under vacuum
- customThe residue is purified on a silica column (eluent Heptane/AcOEt: 9/1 to 7/3) in order
Sources & evidence
- ORD record
- ord-8081cae9c20f4ccd814b1222b3b42991
- Source dataset
- uspto-grants-2009_08
- Patent number
- US07576241B2
Reaction notes
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