Triphenylphosphine → 4-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester

HRID 2308114노트

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HRID 2308114 반응식
C([O:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]O)=C.[CH3:11][O:12][C:13](=[O:25])/[CH:14]=[CH:15]/[C:16]1[CH:21]=[CH:20][C:19]([OH:22])=[C:18]([O:23][CH3:24])[CH:17]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C>O1CCCC1.C1(C)C=CC=CC=1.S(=O)(=O)(O)O.CO>[CH3:11][O:12][C:13](=[O:25])[CH:14]=[CH:15][C:16]1[CH:21]=[CH:20][C:19]([O:22][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][OH:3])=[C:18]([O:23][CH3:24])[CH:17]=1

참가 물질

9

반응물 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 5357283Methyl FerulateHCID 220261996-(Ethenyloxy)-1-hexanol

생성물 1

HCID 541470624-(6-Hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester수율 82.8%

시약·촉매·용매 4

HCID 1118Sulfuric Acid촉매HCID 887Methanol용매HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

3.92 ml (25.2 mmol) of 1,6-hexanediol vinyl ether were added to a solution of 5.0 g (24.0 mmol) of (E)-4-hydroxy-3-methoxycinnamic acid methyl ester and 6.61 g (25.2 mmol) of triphenylphosphine in 150 ml of tetrahydrofuran. The colourless solution was subsequently cooled to 0° C. and then 11.5 ml (25.3 mmol) of a 40% solution of azodicarboxylic acid diethyl ester in toluene were added dropwise thereto over a period of 30 minutes. The mixture was subsequently allowed to react first for 30 minutes at 0° C. and then for 22.5 hours at room temperature. 150 ml of methanol and 10 drops of concentrated sulfuric acid were then added to the reaction solution and the mixture was stirred for 1.5 hours. The reaction mixture was then extracted using ethyl acetate and water. The ethyl acetate was washed with a saturated sodium bicarbonate solution and repeatedly with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated by evaporation. The resulting residue was purified by column chromatography using silica gel (470 g) using toluene:ethyl acetate (1:1) as eluant. Recrystallisation from ethyl acetate:hexane (3:5) gave 6.13 g of 4-(6-hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester.

후처리

  1. customto react first for 30 minutes at 0° C.
  2. waitfor 22.5 hours at room temperature
  3. extractionThe reaction mixture was then extracted
  4. washThe ethyl acetate was washed with a saturated sodium bicarbonate solution and repeatedly with saturated sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation
  8. customThe resulting residue was purified by column chromatography
  9. customRecrystallisation from ethyl acetate:hexane (3:5)

출처 및 근거

ORD 기록
ord-a758a1d13ca64147b33057e1edbe1525
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06833421B1

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