2-Butene, 1-bromo-3-methyl- → 2-Butoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine

HRID 894412Notes

Reaction equation

HRID 894412 reaction equation
[CH2:1](Br)[CH:2]=[C:3]([CH3:5])[CH3:4].[CH3:7][C:8]1[O:9][CH2:10][CH2:11][N:12]=1.[CH3:13][CH2:14][CH2:15][CH2:16][O-:17].[Na+]>C(Cl)Cl.C(O)CCC>[CH2:16]([O:17][C:8]1([CH3:7])[N:12]([CH2:1][CH:2]=[C:3]([CH3:5])[CH3:4])[CH2:11][CH2:10][O:9]1)[CH2:15][CH2:14][CH3:13]

Participants

6

Reactant 3

HCID 700922-Butene, 1-bromo-3-methyl-HCID 707132-Methyl-2-oxazolineHCID 23669364Sodium n-butylate

Product 1

HCID 204742582-Butoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidineYield 59%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 6344DichloromethaneSolvent

Procedure

14.9 g (0.1 mol) of prenyl bromide and 8.5 g (0.1 mol) of 2-methyl-oxazoline were stirred in 50 ml of methylene chloride at 25° C. for 2 hours and the mixture was treated with 0.11 mol of a sodium butylate solution in n-butanol at 40° C. for 1 hour and worked up in the customary manner. 13.4 g (59 mmols, 59%) of 2-butoxy-2-methyl-3-(3-methyl-2-butenyl)-oxazolidine were obtained by distillation at a boiling point 78°-80° C./0.3 mm Hg.

Sources & evidence

ORD record
ord-78e1a38a124c44999ed74f4911a3ef01
Source dataset
uspto-grants-1981_08
Patent number
US04283544

Reaction notes

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