Hydrochloric Acid → 3-{2-Ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propenyl]-phenyl}-acrylic acid

HRID 2240816ノート

反応式

HRID 2240816 の反応式
[CH3:1][C:2]1[S:6][C:5]([C:7](=[O:9])[CH3:8])=[C:4]2[CH2:10][CH2:11][C:12]([CH3:15])([CH3:14])[CH2:13][C:3]=12.[CH2:16]([C:18]1[CH:23]=[C:22]([CH:24]=O)[CH:21]=[C:20]([CH3:26])[C:19]=1[CH:27]=[CH:28][C:29]([OH:31])=[O:30])[CH3:17].Cl>[OH-].[Na+]>[CH2:16]([C:18]1[CH:23]=[C:22]([CH:24]=[CH:8][C:7](=[O:9])[C:5]2[S:6][C:2]([CH3:1])=[C:3]3[CH2:13][C:12]([CH3:15])([CH3:14])[CH2:11][CH2:10][C:4]=23)[CH:21]=[C:20]([CH3:26])[C:19]=1[CH:27]=[CH:28][C:29]([OH:31])=[O:30])[CH3:17]

参加物

5

反応物 3

HCID 313Hydrochloric AcidHCID 574374241-(3,5,5-Trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanoneHCID 765393093-(2-Ethyl-4-formyl-6-methyl-phenyl)-acrylic acid

生成物 1

HCID 671896023-{2-Ethyl-6-methyl-4-[3-oxo-3-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propenyl]-phenyl}-acrylic acid収率 61.1%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

実験手順

A solution of 1-(3,5,5-trimethyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-ethanone (355 mg, 1.55 mmol) and 3-(2-ethyl-4-formyl-6-methyl-phenyl)-acrylic acid (373 mg, 1.70 mmol, Aldehyde 5) in methanolic NaOH (8 mL, 10 g NaOH in 100 mL methanol) is stirred at rt for 3 h before it is carefully acidified to pH 1 by adding 2 N aq. HCl. The mixture is extracted twice with DCM, the organic extracts are washed with water and brine, dried over MgSO4, filtered and evaporated. The crude product is crystallised from acetonitrile (120 mL) to give 3-{2-ethyl-6-methyl-4-[3-oxo-3-(3,5,5-tri methyl-4,5,6,7-tetrahydro-benzo[c]thiophen-1-yl)-propenyl]-phenyl}-acrylic acid (400 mg) as yellow crystals; LC-MS: tR=1.17 min, [M+1]=423.34; 1H NMR (CDCl3): δ 7.97 (d, J=16.4 Hz, 1H), 7.68 (d, J=15.2 Hz, 1H), 7.33 (s, 2H), 7.28 (d, J=15.8 Hz, 1H), 6.13 (d, J=15.8 Hz, 1H), 3.16 (t, J=7.0 Hz, 2H), 2.77 (q, J=7.6 Hz, 2H), 2.41 (s, 3H), 2.39 (s, 3H), 2.32 (s, 2H), 1.57 (t, J=6.4 Hz, 2H), 1.24 (t, J=7.6 Hz, 3H), 1.00 (s, 6H).

後処理

  1. extractionThe mixture is extracted twice with DCM
  2. washthe organic extracts are washed with water and brine
  3. dry with materialdried over MgSO4
  4. filtrationfiltered
  5. customevaporated
  6. customThe crude product is crystallised from acetonitrile (120 mL)

出典と根拠

ORDレコード
ord-c8be1da7f6c449ac976bfd417abff5ff
出典データセット
uspto-grants-2010_05
特許番号
US07723378B2

反応ノート

読み込み中…