Acetonitrile → acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester

HRID 42732

반응식

HRID 42732 반응식
[O:1]=[C:2]1[C:15]2[CH:14]=[C:13]([O:16][CH2:17][C:18]([OH:20])=[O:19])[CH:12]=[CH:11][C:10]=2[S:9][C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.C(#N)C.[OH:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32].[CH2:34](OCC1OC1)[CH:35]1[O:37][CH2:36]1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(C1C=C(C)C=C(C(C)(C)C)C=1O)(C)(C)C.CC(N(C)C)=O>[OH:37][CH:35]([CH2:36][O:19][C:18](=[O:20])[CH2:17][O:16][C:13]1[CH:12]=[CH:11][C:10]2[S:9][C:8]3[C:3](=[CH:4][CH:5]=[CH:6][CH:7]=3)[C:2](=[O:1])[C:15]=2[CH:14]=1)[CH2:34][O:24][CH2:25][CH2:26][CH2:27][CH2:28][O:29][C:30](=[O:33])[CH:31]=[CH2:32]

참가 물질

7

반응물 3

HCID 6342AcetonitrileHCID 30198532-(Carboxymethoxy)thioxanthoneHCID 223231504-Hydroxybutylacrylate glycidylether

생성물 1

HCID 58325515acrylic acid 4-{2-hydroxy-3-[2-(9-oxo-9H-thioxanthen-2-yloxy)-acetoxy]-propoxy}-butyl ester수율 144.2%

시약·촉매·용매 3

HCID 314042,6-Di-tert-butyl-4-methylphenol촉매HCID 74236Tetrabutylammonium Bromide촉매HCID 31374Dimethylacetamide용매

실험 절차

A reaction mixture containing (9-oxo-9H-thioxanthen-2-yloxy)acetic acid (4.0 g, 14 mmol), acetonitrile (55 ml), dimethylacetamide (10 mL), tetrabutylammonium bromide (0.5 g, 1.4 mmol) and 2,6-di-tert-butyl-4-methylphenol (0.03 g, 0.114 mmol) was heated to reflux. At this temperature 4-hydroxybutylacrylate glycidylether (2.3 g, 11.4 mmol) was added and the mixture was allowed to stir at reflux temperature for 16 hours. The mixture was cooled to room temperature and the solvent was evaporated under reduced pressure to provide 8.0 g of a yellow oil. The product was purified on a Prochrom LC80 Column using Kromasil Si 60A 10 μm as silica and dichloromethane/ethyl acetate (60/40) as eluent, to afford 1.8 g of a yellow oil.

후처리

  1. temperaturewas heated to reflux
  2. temperatureat reflux temperature for 16 hours
  3. customthe solvent was evaporated under reduced pressure

출처 및 근거

ORD 기록
ord-0d06cbb7a63845c398af753e17c01870
출처 데이터셋
uspto-grants-2013_09
특허 번호
US08536217B2

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