Triphenylphosphine → 4-((2,2-dimethoxy)ethyl)-1-((2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenyloxy)benzene

HRID 128787

반응식

HRID 128787 반응식
[CH3:1]/[C:2](=[CH:5]\[CH2:6][CH2:7][CH2:8][CH2:9][C:10]1[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]=1[CH3:18])/[CH2:3][OH:4].[CH3:19][O:20][CH:21]([O:30][CH3:31])[CH2:22][C:23]1[CH:28]=[CH:27][C:26](O)=[CH:25][CH:24]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[CH3:31][O:30][CH:21]([O:20][CH3:19])[CH2:22][C:23]1[CH:24]=[CH:25][C:26]([O:4][CH2:3]/[C:2](/[CH3:1])=[CH:5]/[CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[C:15]([CH3:17])([CH3:16])[CH2:14][CH2:13][CH2:12][C:11]=2[CH3:18])=[CH:27][CH:28]=1

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 19375035(2E)-2-Methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenolHCID 193750574-(2,2-Dimethoxyethyl)phenol

생성물 1

HCID 193751194-((2,2-dimethoxy)ethyl)-1-((2E)-2-methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenyloxy)benzene수율 91.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

(2E)-2-Methyl-7-(2,6,6-trimethyl-1-cyclohexen-1-yl)-2-heptenol (1.5 g), 4-((2,2-dimethoxy)ethyl)phenol (1.1 g) and triphenylphosphine (1.59 g) are dissolved in THF (10 ml) and the solution cooled to 0°. Diethyl azodicarboxylate (1.05 ml, in 9 ml THF) is added dropwise with stirring, and the mixture is allowed to warm to room temperature and stirred overnight. The reaction mixture is concentrated and the residue is chromatographed with dichloromethane to provide 4-((2,2-dimethoxy)ethyl)-1-((2E)-2-methyl-7-(2,6,6-trimethyl- 1-cyclohexen-1-yl)-2-heptenyloxy)benzene as a pale yellow oil (2.27 g). This material is reacted with glyoxylic acid and morpholine hydrochloride by the method of Example 2 above, purified by chromatography with 7% ether in dichloromethane, and recrystallized from hexane-dichloromethane to provide the title compound as a white solid, mp 119°-121° (1.0 g).

후처리

  1. temperaturethe solution cooled to 0°
  2. stirringstirred overnight
  3. concentrationThe reaction mixture is concentrated
  4. customthe residue is chromatographed with dichloromethane

출처 및 근거

ORD 기록
ord-bddd97da5b604bebbb68997091d0006b
출처 데이터셋
uspto-grants-1995_11
특허 번호
US05464865

연결된 노트

불러오는 중…