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

HRID 128787ノート

反応式

HRID 128787 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

(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).

後処理

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

出典と根拠

ORDレコード
ord-bddd97da5b604bebbb68997091d0006b
出典データセット
uspto-grants-1995_11
特許番号
US05464865

反応ノート

読み込み中…