Hydrochloric Acid → HCID 20745898, 화합물

HRID 2308130노트

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HRID 2308130 반응식
[CH3:1][O:2][C:3](=[O:32])/[CH:4]=[CH:5]/[C:6]1[CH:11]=[CH:10][C:9]([O:12][CH2:13][C:14]2[CH:19]=[C:18]([CH2:20]O)[CH:17]=[C:16]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][Cl:29])[CH:15]=2)=[C:8]([O:30][CH3:31])[CH:7]=1.[CH3:33][O:34][C:35](=[O:49])/[C:36](/[C:47]#[N:48])=[CH:37]/[C:38]1[CH:43]=[CH:42][C:41]([OH:44])=[C:40]([O:45][CH3:46])[CH:39]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(OC(N=NC(OCC)=O)=O)C.Cl>O1CCCC1.C1(C)C=CC=CC=1>[CH3:33][O:34][C:35](=[O:49])/[C:36](/[C:47]#[N:48])=[CH:37]/[C:38]1[CH:43]=[CH:42][C:41]([O:44][CH2:20][C:18]2[CH:19]=[C:14]([CH2:13][O:12][C:9]3[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:32])=[CH:7][C:8]=3[O:30][CH3:31])[CH:15]=[C:16]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][Cl:29])[CH:17]=2)=[C:40]([O:45][CH3:46])[CH:39]=1

참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 790176HCID 790176, 화합물HCID 20745900HCID 20745900, 화합물

생성물 1

HCID 20745898HCID 20745898, 화합물수율 79%

시약·촉매·용매 2

HCID 1140Toluene용매HCID 8028Tetrahydrofuran용매

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온도
0 °C

실험 절차

1 g (2.2 mmol) (E)-3-[4-[3-[(6-chlorohexyl)oxy]-5-[hydroxymethyl]benzyloxy]-3-methoxyphenyl]acrylic acid methyl ester was added to a solution of 0.62 g (2.7 mmol) 2-cyano-(E)-3-(4-hydroxy-3-methoxyphenyl)acrylic acid methyl ester and 0.73 g (2.7 mmol) triphenylphosphine in 10 ml tetrahydrofuran. The solution was cooled to 0°C. and then 1.1 ml (2.7 mmol) of a solution of azodicarboxlic acid diethyl ester in toluene were added dropwise. The mixture was allowed to react for 1 hour at 0° C. and then it was poured into an ice cold 1 M solution of HCl. The mixture was extracted three times with tert.-butyl-methylether/ethyl acetate. The organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water, dried over magnesium sulfates filtered and concentrated in vacuum. The solid residue was first treated with diethylether, filtered and then it was recrystallized twice from tert.-butyl-methylether to give 1.1 g (79%) of (E)-3-[4-[[3-[(6-Chlorohexyl)oxy]-5-[[2-methoxy-4-[(E)-2-(methoxycarbonyl)vinyl]phenoxy]methyl]benzyl]oxy)-3-methoxyphenyl]-2-cyanoacrylic acid methyl ester in form of slightly yellow crystals.

후처리

  1. customto react for 1 hour at 0° C.
  2. extractionThe mixture was extracted three times with tert.-butyl-methylether/ethyl acetate
  3. washThe organic phase was washed with a saturated sodium bicarbonate solution and repeatedly with water
  4. dry with materialdried over magnesium sulfates
  5. filtrationfiltered
  6. concentrationconcentrated in vacuum
  7. additionThe solid residue was first treated with diethylether
  8. filtrationfiltered
  9. customit was recrystallized twice from tert.-butyl-methylether

출처 및 근거

ORD 기록
ord-f15e0920f7334896b5eca2d3644439f8
출처 데이터셋
uspto-grants-2004_12
특허 번호
US06833421B1

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