4,4-Dimethyl-2-(2-methoxyphenyl)oxazoline → 4,4-Dimethyl-2-[2-(8-phenyloctyl)phenyl]-4,5-dihydro-1,3-oxazole

HRID 2082601ノート

反応式

HRID 2082601 の反応式
[I-].[CH2:2]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[C:20]1[O:21][CH2:22][C:23]([CH3:27])([CH3:26])[N+:24]=1C)[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH3:13].[CH2:28](C1C=CC=CC=1C=O)[CH2:29]CCCCCCCCCC.C1(CCCCCCCC[Mg]Br)C=CC=CC=1.COC1C=CC=CC=1C1OCC(C)(C)N=1>O1CCCC1>[C:10]1([CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[C:20]2[O:21][CH2:22][C:23]([CH3:26])([CH3:27])[N:24]=2)[CH:11]=[CH:12][CH:13]=[CH:29][CH:28]=1

参加物

6

反応物 4

HCID 3331894,4-Dimethyl-2-(2-methoxyphenyl)oxazolineHCID 140975702-(2-Dodecylphenyl)-3,4,4-trimethyl-4,5-dihydro-1,3-oxazol-3-ium iodideHCID 140975722-DodecylbenzaldehydeHCID 178419677HCID 178419677、化合物

生成物 1

HCID 156174024,4-Dimethyl-2-[2-(8-phenyloctyl)phenyl]-4,5-dihydro-1,3-oxazole

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 8-phenyloctylmagnesium bromide (from 24.25 mmoles of 8-phenyloctyl bromide and 21.27 mmoles of magnesium) in distilled tetrahydrofuran (40 ml) was added 2-(2-methoxyphenyl)-4,4-dimethyloxazoline (17.10 mmoles) in tetrahydrofuran (20 ml). After stirring for 24 hours, the reaction mixture was similarly worked up to yield 2-[2-(8-phenyloctyl)phenyl]4,4-dimethyloxazoline as an oil. A solution of the oxazoline (11.58 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 76.5°-78° C.). To an ice cold solution of the iodide (9.46 mmoles) in methanol (35 ml) was added in portions sodium borohydride (9.20 mmoles). Treatment of the reaction mixture as in Example 1(c) results in the isolation of the desired product as an oil.

出典と根拠

ORDレコード
ord-2cd4b8ccb5ef4495a2ce89e57f65dc06
出典データセット
uspto-grants-1993_02
特許番号
US05189226

反応ノート

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