4,4-Dimethyl-2-(2-methoxyphenyl)oxazoline → 2-[2-(4-(4-Butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline

HRID 2351060ノート

反応式

HRID 2351060 の反応式
[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][Mg]Br)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4].CO[C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=1[C:25]1[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=1>O1CCCC1>[CH2:1]([C:5]1[CH:10]=[CH:9][C:8]([CH2:11][CH2:12][CH2:13][CH2:14][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[C:25]2[O:26][CH2:27][C:28]([CH3:31])([CH3:30])[N:29]=2)=[CH:7][CH:6]=1)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 2

HCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 178440843HCID 178440843、化合物

生成物 1

HCID 198479512-[2-(4-(4-Butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

実験手順

Following the procedures of Example 1(a), (b) and (c), to 4-(4-butylphenyl)butylmagnesium bromide (from 21.47 mmoles of 4-(4-butylphenyl)butyl bromide and 18.96 mmoles of magnesium) in distilled tetrahydrofuran (35 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (16.32 mmoles) in tetrahydrofuran (15 ml). Workup of the reaction mixture furnished 2-[2-(4-(4-butylphenyl)butyl)phenyl]-4,4-dimethyloxazoline as an oil. A solution of the oxazoline (14.41 mmoles) in methyl iodide (20 ml) was refluxed under argon for 18 hours. Removal of the volatiles afforded the corresponding 3,4,4-trimethyloxazolinium iodide as a white solid (mp 91°-94° C.). To an ice cold solution of the iodide (14.07 mmoles) in methanol was added in portions sodium borohydride (14.30 mmoles). Similar treatment of the reaction mixture resulted in the isolation of the desired benzaldehyde product as an oil.

出典と根拠

ORDレコード
ord-481df7aa66de4eeaac8bb5733d2d45e4
出典データセット
uspto-grants-1989_10
特許番号
US04871771

反応ノート

読み込み中…