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 2240816Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2240816
[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]

Komponenten

5

Edukt 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

Produkt 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 acidAusbeute 61,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

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).

Aufarbeitung

  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)

Quellen und Nachweise

ORD-Eintrag
ord-c8be1da7f6c449ac976bfd417abff5ff
Quelldatensatz
uspto-grants-2010_05
Patentnummer
US07723378B2

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