Hydrochloric Acid → HCID 20745898、化合物

HRID 2308130ノート

反応式

HRID 2308130 の反応式
[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

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 790176HCID 790176、化合物HCID 20745900HCID 20745900、化合物

生成物 1

HCID 20745898HCID 20745898、化合物収率 79%

試薬・触媒・溶媒 2

HCID 1140Toluene溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-f15e0920f7334896b5eca2d3644439f8
出典データセット
uspto-grants-2004_12
特許番号
US06833421B1

反応ノート

読み込み中…