Sodium Hydroxide → 3-{4-[3-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2,6-dimethyl-phenyl}-propionic acid

HRID 1013442ノート

反応式

HRID 1013442 の反応式
[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH3:9])=[C:5]2[CH2:11][CH2:12][C:13]([CH3:16])([CH3:15])[CH2:14][C:4]=12)[CH3:2].[CH:17]([C:19]1[CH:24]=[C:23]([CH3:25])[C:22]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:21]([CH3:31])[CH:20]=1)=O.[OH-].[Na+]>CO.Cl>[CH2:1]([C:3]1[S:7][C:6]([C:8](=[O:10])[CH:9]=[CH:17][C:19]2[CH:24]=[C:23]([CH3:25])[C:22]([CH2:26][CH2:27][C:28]([OH:30])=[O:29])=[C:21]([CH3:31])[CH:20]=2)=[C:5]2[CH2:11][CH2:12][C:13]([CH3:15])([CH3:16])[CH2:14][C:4]=12)[CH3:2]

参加物

6

反応物 3

HCID 14798Sodium HydroxideHCID 574374043-(4-Formyl-2,6-dimethyl-phenyl)-propionic acidHCID 574374251-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone

生成物 1

HCID 673169693-{4-[3-(3-Ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2,6-dimethyl-phenyl}-propionic acid収率 86.4%

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 887Methanol溶媒

実験手順

A solution of 1-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (400 mg, 1.69 mmol), 3-(4-formyl-2,6-dimethyl-phenyl)-propionic acid (419 mg, 2.03 mmol) and NaOH (1.7 g, 42.5 mmol) in methanol (17 mL) is stirred at 75° C. for 75 min before it is diluted with 1 N aq. HCl and extracted twice with EA. The organic extracts are dried over MgSO4, filtered and evaporated. The crude product is purified by CC on silica gel eluting with DCM containing 6% of methanol to give 3-{4-[3-(3-ethyl-5,5-dimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-3-oxo-propenyl]-2,6-dimethyl-phenyl}-propionic acid (620 mg) as a pale yellow solid; LC-MS: tR=1.17 min; [M+1]=425.34; 1H NMR (CDCl3): δ 7.68 (d, J=15.8 Hz, 1H), 7.28 (s, 2H), 7.27 (d, J=15.8 Hz, 1H), 3.18 (t, J=7.0 Hz, 2H), 3.06-2.98 (m, 2H), 2.78 (q, J=7.6 Hz, 2H), 2.54-2.48 (m, 2H), 2.39 (s, 6H), 2.34 (s, 2H), 1.58 (t, J=7.0 Hz, 2H), 1.32 (t, J=7.6 Hz, 3H).

後処理

  1. extractionextracted twice with EA
  2. dry with materialThe organic extracts are dried over MgSO4
  3. filtrationfiltered
  4. customevaporated
  5. customThe crude product is purified by CC on silica gel eluting with DCM containing 6% of methanol

出典と根拠

ORDレコード
ord-657c28ef7a6a429aa7918709a88b4841
出典データセット
uspto-grants-2011_07
特許番号
US07981924B2

反応ノート

読み込み中…