ホームMCPワークベンチSkills
ホームワークベンチ通知マイページ
llms.txt · MCPガイドプライバシーポリシー · 利用規約 · サポートv1.8.0
  1. ホーム
  2. /反応

Sulfuric Acid → 5-[(3-Carboxyphenyl)carbonyl]-2-[6-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]hexyloxy]benzenepropanoic Acid

HRID 1647987
ノート
印刷プレビュー

反応式

HRID 1647987 の反応式
C([O:3][C:4](=[O:48])[CH2:5][CH2:6][C:7]1[CH:12]=[C:11]([C:13]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23]CC)=[O:22])[CH:16]=2)=[O:14])[CH:10]=[CH:9][C:8]=1[O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]1[CH:44]=[CH:43][C:37]2[C:38](=[O:42])[CH2:39][CH2:40][O:41][C:36]=2[C:35]=1[CH2:45][CH2:46][CH3:47])C.O.[OH-].[Li+].S(=O)(=O)(O)O.C(OCC)(=O)C>C1COCC1.O>[C:21]([C:17]1[CH:16]=[C:15]([C:13]([C:11]2[CH:10]=[CH:9][C:8]([O:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][O:33][C:34]3[CH:44]=[CH:43][C:37]4[C:38](=[O:42])[CH2:39][CH2:40][O:41][C:36]=4[C:35]=3[CH2:45][CH2:46][CH3:47])=[C:7]([CH2:6][CH2:5][C:4]([OH:48])=[O:3])[CH:12]=2)=[O:14])[CH:20]=[CH:19][CH:18]=1)([OH:23])=[O:22]
参加物実験手順出典と根拠反応ノート

参加物

7

反応物 4

HCID 1118Sulfuric AcidHCID 8857Ethyl AcetateHCID 168937Lithium hydroxide, monohydrateHCID 536732502-[6-[(2,3-dihydro-4-oxo-8-propyl-4H-1-benzopyran-7-yl)oxy]hexyloxy]-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester

生成物 1

HCID 199220415-[(3-Carboxyphenyl)carbonyl]-2-[6-[(3,4-dihydro-4-oxo-8-propyl-2H-1-benzopyran-7-yl)oxy]hexyloxy]benzenepropanoic Acid

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

A mixture of 0.144 g (0.70 mmol) of 2,3-dihydro-7-hydroxy-8-propyl-4H-1-benzopyran-4-one, 0.371 g (0.70 mmol) of 2-[(6-bromohexyl)oxy]-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester, 0.479 g (3.47 mmol) of anhydrous granular potassium carbonate and 13.1 mL of 2-butanone was stirred and refluxed for 18 hr. The resulting slurry was filtered with suction and the solids washed thoroughly with ethyl acetate. The filtrate and washes were combined and concentrated in vacuo and the residue was purified by flash chromatography on 75 g of silica gel, eluting with 3:1 hexane-ethyl acetate, giving 0.37 g (80.6%) of 2-[6-[(2,3-dihydro-4-oxo-8-propyl-4H-1-benzopyran-7-yl)oxy]hexyloxy]-5-[[3-(ethoxycarbonyl)phenyl]carbonyl]benzenepropanoic acid ethyl ester as a white solid, mp 58°-59.5° C. A mixture of 0.331 g (0.50 mmol) of this ester in 6 mL of THF and 6 mL of water was treated with 64.7 mg (1.54 mmol) of lithium hydroxide monohydrate and the resulting mixture was stirred for 25.5 hr at room temperature, before being acidified with 17 mL of 3N aqueous sulfuric acid. Work-up with ethyl acetate in the usual manner gave a crude product which was recrystallized from hexane-ethyl acetate affording 0.242 g (79.7%) of the title compound as a white solid, mp 169°-172° C.

出典と根拠

ORDレコード
ord-ce3a7bb0067d4b67a6c9dc0b2d21d9c1
出典データセット
uspto-grants-1995_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05434186

反応ノート

読み込み中…

このページの内容参加物実験手順出典と根拠反応ノート