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

HRID 42732

反応式

HRID 42732 の反応式
[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]

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 314042,6-Di-tert-butyl-4-methylphenol触媒HCID 74236Tetrabutylammonium Bromide触媒HCID 31374Dimethylacetamide溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-0d06cbb7a63845c398af753e17c01870
出典データセット
uspto-grants-2013_09
特許番号
US08536217B2

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