2-Phenylethanol → HCID 21036281, 화합물

HRID 1789645노트

반응식

HRID 1789645 반응식
[OH:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]([CH3:14])=[CH:10][C:11]([OH:13])=[O:12].C1(N=C=NC2CCCCC2)CCCCC1.ON1C2C=CC=CC=2N=N1.[CH2:40](O)[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1>O1CCCC1.CN(C)C1C=CN=CC=1>[CH2:40]([O:12][C:11](=[O:13])/[CH:10]=[C:9](/[C:3]1[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=1[OH:1])\[CH3:14])[CH2:41][C:42]1[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=1

참가 물질

7

반응물 4

HCID 60542-PhenylethanolHCID 10868DicyclohexylcarbodiimideHCID 757711-HydroxybenzotriazoleHCID 66933108HCID 66933108, 화합물

생성물 1

HCID 21036281HCID 21036281, 화합물

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
22 °C

실험 절차

To a 0° C. solution of 9.7 g (0.050 mol) of 3-(2,4-dihydroxyphenyl)but-2-enoic acid in 500 mL of anhydrous tetrahydrofuran (THF) is added 10.3 g (0.050 mol) of 1,3-dicyclohexylcarbodiimide (DCC). After stirring for 10 min, 6.8 g (0.050 mol) of 1-hydroxybenzotriazole (HOBt), 5.5 g (0.045 mol) of phenethyl alcohol and 1.1 g (0.009 mol) of 4-(dimethylamino)pyridine (DMAP) is added and stirred at 0° C. for 1 h, warmed to 22° C. and stirred for an additional 72 h. The mixture is cooled to 0° C., filtered and the solvent is removed under vacuum. The residue is diluted with ethyl acetate and washed three times with saturated sodium bicarbonate, followed by 10% citric acid and brine. The organic layer is dried over anhydrous magnesium sulfate, filtered and concentrated under vacuum to give (E)-3-(2,4-dihydroxyphenyl)-but-2-enoic acid phenethyl ester as a yellow oil that is purified by flash chromatography.

후처리

  1. stirringstirred at 0° C. for 1 h
  2. stirringstirred for an additional 72 h
  3. temperatureThe mixture is cooled to 0° C.
  4. filtrationfiltered
  5. customthe solvent is removed under vacuum
  6. additionThe residue is diluted with ethyl acetate
  7. washwashed three times with saturated sodium bicarbonate
  8. dry with materialThe organic layer is dried over anhydrous magnesium sulfate
  9. filtrationfiltered
  10. concentrationconcentrated under vacuum

출처 및 근거

ORD 기록
ord-29931067ae7f4dd5b8eb596caeb473e3
출처 데이터셋
uspto-grants-2006_07
특허 번호
US07071151B2

반응 노트

불러오는 중…