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

HRID 479927

반응식

HRID 479927 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

반응 조건

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 in the course of 30 minutes. The mixture was subsequently allowed to react first for 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 partitioned between ethyl acetate and water; the organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with saturated sodium chloride solution, dried over magnesium sulfate, filtered and concentrated by evaporation. Chromatography of the residue on 470 g of silica gel using toluene:ethyl acetate 1:1 and subsequent crystallisation from ethyl acetate:hexane 3:5 yielded 6.13 g of 4-(6-hydroxyhexyloxy)-3-methoxycinnamic acid methyl ester.

후처리

  1. customin the course of 30 minutes
  2. customto react first for minutes at 0° C.
  3. customThe reaction mixture was then partitioned between ethyl acetate and water
  4. washthe organic phase 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. customtoluene:ethyl acetate 1:1 and subsequent crystallisation from ethyl acetate:hexane 3:5

출처 및 근거

ORD 기록
ord-178a76a324874034845445edabda7152
출처 데이터셋
uspto-grants-2003_11
특허 번호
US06649230B1

연결된 노트

불러오는 중…