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

HRID 2082601노트

반응식

HRID 2082601 반응식
[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

참가 물질

6

반응물 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, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

출처 및 근거

ORD 기록
ord-2cd4b8ccb5ef4495a2ce89e57f65dc06
출처 데이터셋
uspto-grants-1993_02
특허 번호
US05189226

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