Probucol → 2-Propenoic acid, 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyl ester

HRID 1857891

반응식

HRID 1857891 반응식
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([S:16][C:17]([S:20][C:21]2[CH:26]=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[C:24]([OH:31])=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[CH:22]=2)([CH3:19])[CH3:18])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[C:36]([O:40][CH2:41][CH2:42][CH2:43][CH2:44]O)(=[O:39])[CH:37]=[CH2:38].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O>C1COCC1>[C:36]([O:40][CH2:41][CH2:42][CH2:43][CH2:44][O:11][C:10]1[C:9]([C:12]([CH3:13])([CH3:14])[CH3:15])=[CH:8][C:7]([S:16][C:17]([S:20][C:21]2[CH:22]=[C:23]([C:32]([CH3:35])([CH3:34])[CH3:33])[C:24]([OH:31])=[C:25]([C:27]([CH3:30])([CH3:29])[CH3:28])[CH:26]=2)([CH3:18])[CH3:19])=[CH:6][C:5]=1[C:2]([CH3:1])([CH3:3])[CH3:4])(=[O:39])[CH:37]=[CH2:38]

참가 물질

6

반응물 4

HCID 4912ProbucolHCID 11776TriphenylphosphineHCID 755884-Hydroxybutyl acrylateHCID 220568ethyl N-ethoxycarbonyliminocarbamate

생성물 1

HCID 114678632-Propenoic acid, 4-[4-[[1-[[3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]thio]-1-methylethyl]thio]-2,6-bis(1,1-dimethylethyl)phenoxy]butyl ester수율 28.6%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of probucol (2.58 g, 5 mmol) in THF (50 ML) were added 4-hydroxybutyl acrylate (1.0 ml, 10 mmol), triphenylphosphine (2.62 g, 10 mmol) and diethyl azodicarboxylate (1.57 ml, 10 mmol). The resultant mixture was stirred under nitrogen at reflux over weekend. It was evaporated. Silica gel chromatography (hexanes/dichloromethane 4:1) gave the title compound as a brown oil (0.92 g). 1H-NMR (400 MHz, CDCl3): 7.54 (s, 2H), 7.46 (s, 2H), 6.42 (dd, 1H), 6.14 (dd, 1H), 5.84 (dd, 1H), 5.38 (s, 1H), 4.23 (t, 2H), 3.75 (t, 2H), 1.97 (m, 2H), 1.82 (m, 2H), 1.46 (s, 6H), 1.45 (s, 18H), 1.42 (s, 18H).

후처리

  1. temperatureat reflux over weekend
  2. customIt was evaporated

출처 및 근거

ORD 기록
ord-d8f10de628894393b8c8ea40bf0f428e
출처 데이터셋
uspto-grants-2000_11
특허 번호
US06147250

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