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Triphenylphosphine → methyl (Z)-[4-[3-(4-iodophenyl)-3-[4-(5-methylthiophen-2-yl)phenyl]allyloxy]-2-methylphenoxy]acetate

HRID 1810633
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HRID 1810633 반응식
[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:14][CH:13]=2)=[CH:9]\[CH2:10][OH:11])=[CH:4][CH:3]=1.[CH3:24][C:25]1[CH:35]=[C:34](OC/C=C(/C2C=CC(C#CCN3CCOCC3)=CC=2)\C2C=CC=CC=2)[CH:33]=[CH:32][C:26]=1[O:27][CH2:28][C:29]([OH:31])=[O:30].[C:61]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OC(C)C)=O)=NC(OC(C)C)=O>C1(C)C=CC=CC=1.O1CCCC1>[I:1][C:2]1[CH:7]=[CH:6][C:5](/[C:8](/[C:12]2[CH:17]=[CH:16][C:15]([C:18]3[S:19][C:20]([CH3:23])=[CH:21][CH:22]=3)=[CH:14][CH:13]=2)=[CH:9]\[CH2:10][O:11][C:34]2[CH:33]=[CH:32][C:26]([O:27][CH2:28][C:29]([O:31][CH3:61])=[O:30])=[C:25]([CH3:24])[CH:35]=2)=[CH:4][CH:3]=1
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참가 물질

7

반응물 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 23633918(e)-[2-Methyl-4-[3-[4-[3-(morpholin-4-yl)propynyl]phenyl]-3-phenylallyloxy]phenoxy]acetic acidHCID 67145828(z)-3-(4-Iodophenyl)-3-[4-(5-methylthiophen-2-yl)phenyl]allyl alcohol

생성물 1

HCID 86629294methyl (Z)-[4-[3-(4-iodophenyl)-3-[4-(5-methylthiophen-2-yl)phenyl]allyloxy]-2-methylphenoxy]acetate

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매2회

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온도
0 °C

실험 절차

The above allyl alcohol (0.65 g, 1.50 mmol), methyl (4-hydroxy-2-methylphenoxy)-acetate (0.33 g, 1.68 mmol; example 2) and triphenylphosphine (0.48 g, 1.83 mmol) were dissolved in a mixture of anhydrous toluene (30 mL) and tetrahydrofuran (10 mL). The mixture was cooled to 0° C., kept under nitrogen and a degassed solution of diisopropyl azodicarboxylate (0.35 mL, 1.77 mmol) in anhydrous tetrahydrofuran (5 mL) was added dropwise during 10 min. The reaction mixture was allowed to warm up the ambient temperature with the bath and then was stirred overnight. The solvents were evaporated in vacuo and the residue was submitted to flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 6:1) affording methyl (Z)-[4-[3-(4-iodophenyl)-3-[4-(5-methylthiophen-2-yl)phenyl]-allyloxy]-2-methylphenoxy]acetate as solid mass.

후처리

  1. temperatureto warm up the ambient temperature with the bath
  2. customThe solvents were evaporated in vacuo

출처 및 근거

ORD 기록
ord-405ac007da1044f1894679772c8c059f
출처 데이터셋
uspto-grants-2013_01
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08362016B2

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