2-(Chloromethyl)-1-butene → HCID 23453431, compound

HRID 1277735Notes

Reaction equation

HRID 1277735 reaction equation
[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10][CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([Li])CCC.Cl[CH2:26][C:27]([CH2:29][CH3:30])=[CH2:28]>O1CCCC1>[CH2:1]([N:8]1[CH2:13][CH2:12][C:11]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)([CH2:28][C:27]([CH2:29][CH3:30])=[CH2:26])[CH:10]=[CH:9]1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 899602-(Chloromethyl)-1-buteneHCID 5636091-Benzyl-4-phenyl-1,2,3,6-tetrahydropyridineHCID 178418339Butyllithium

Product 1

HCID 23453431HCID 23453431, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 1-benzyl-4-phenyl-1,2,5,6-tetrahydropyridine in tetrahydrofuran containing n-butyl lithium is added to a solution of 3-chloro-2-ethylpropene in tetrahydrofuran. The reaction is carried out according to the procedure of Example 1 to give 1-benzyl-4-phenyl-4-(2-ethylallyl)-1,4,5,6-tetrahydropyridine. The later compound is reacted with phosphoric acid and formic acid to give, after treatment with sodium hydroxide, 2-benzyl-3,4-dehydro-5-phenyl-7-ethylmorphan. Catalytic hydrogenation of the latter compound provides 2-benzyl-5-phenyl-7-ethylmorphan.

Sources & evidence

ORD record
ord-88db6a4f39d6417cade0f6859f4fafa5
Source dataset
uspto-grants-1981_07
Patent number
US04278797

Reaction notes

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