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Tetrahydrofuran → methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(pyridin-2-ylethynyl)phenyl]allyloxy]-phenoxy]acetate

HRID 549842
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HRID 549842 반응식
[CH3:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14]/[CH:15]=[C:16](/[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)\[C:17]2[CH:22]=[CH:21][C:20]([C:23]#[C:24][CH2:25][N:26]3CCO[CH2:28][CH2:27]3)=[CH:19][CH:18]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=[O:7].[C:39](C1C=CC=CN=1)#[CH:40].O1CCC[CH2:48]1>C(N(CC)CC)C.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cu]I>[CH3:1][C:2]1[CH:12]=[C:11]([O:13][CH2:14]/[CH:15]=[C:16](/[C:32]2[CH:37]=[CH:36][C:35]([CH3:38])=[CH:34][CH:33]=2)\[C:17]2[CH:18]=[CH:19][C:20]([C:23]#[C:24][C:25]3[CH:40]=[CH:39][CH:28]=[CH:27][N:26]=3)=[CH:21][CH:22]=2)[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([O:8][CH3:48])=[O:7]
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참가 물질

7

반응물 3

HCID 8028TetrahydrofuranHCID 137268EthynylpyridineHCID 23633919(Z)-[2-Methyl-4-[3-(4-methylphenyl)-3-[4-[3-(morpholin-4-yl)propynyl]phenyl]allyloxy]-phenoxy]acetic Acid

생성물 1

HCID 86629288methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(pyridin-2-ylethynyl)phenyl]allyloxy]-phenoxy]acetate

시약·촉매·용매 3

HCID 24350
Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)
촉매
HCID 178418397HCID 178418397, 화합물촉매
HCID 8471Triethylamine용매

실험 절차

A solution of methyl (Z)-[2-methyl-4-[3-(4-iodophenyl)-3-(4-methylphenyl)]allyloxy]-phenoxy]acetate (310 mg, 0.587 mmol; example 3) in a mixture of tetrahydrofuran (9 mL) and triethylamine (9 mL) was degassed and 2-ethynylpyridine (121 mg, 1.17 mmol) was added in argon atmosphere. The solution was cooled down; tetrakis(triphenylphosphine)palladium (55 mg, 0.047 mmol) and copper(I) iodide (17.8 mg, 0.094 mmol) were added. The reaction mixture was stirred at ambient temperature for 48 h, then evaporated in vacuo and the residue was dissolved in ethyl acetate (20 mL). The solution was washed with water (3×15 mL), dried with anhydrous magnesium sulphate and evaporated in vacuo. The residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3) yielding methyl (Z)-[2-methyl-4-[3-(4-methylphenyl)-3-[4-(pyridin-2-ylethynyl)phenyl]allyloxy]-phenoxy]acetate.

후처리

  1. customwas degassed
  2. temperatureThe solution was cooled down
  3. customevaporated in vacuo
  4. dissolutionthe residue was dissolved in ethyl acetate (20 mL)
  5. washThe solution was washed with water (3×15 mL)
  6. dry with materialdried with anhydrous magnesium sulphate
  7. customevaporated in vacuo
  8. customThe residue was purified by flash column chromatography (silica gel Fluka 60, hexanes/ethyl acetate 7:3)

출처 및 근거

ORD 기록
ord-2f7b6b17806c4ab1ad47261b92c52fbf
출처 데이터셋
uspto-grants-2011_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07943613B2

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