Ethanol → 2H-Thieno(2,3-c)(1)benzopyran-9-ol, 1,4-dihydro-7-(1,2-dimethylheptyl)-2,4,4-trimethyl-

HRID 1657659Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1657659
C[CH:2]1[S:6][CH:5]([C:7](OCC)=O)[C:4](=O)[CH2:3]1.[CH3:13][CH:14]([CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH:15]([C:17]1[CH:18]=[C:19]([OH:24])[CH:20]=[C:21]([CH:23]=1)[OH:22])[CH3:16].O[C:31]1C2C3CC(C)SC=3C(=O)OC=2C=C(C(C(C)CCCCC)C)C=1.[CH2:55](O)[CH3:56]>>[CH3:7][CH:5]1[S:6][C:2]2[C:55]([CH3:56])([CH3:31])[O:22][C:21]3[CH:23]=[C:17]([CH:15]([CH:14]([CH3:13])[CH2:25][CH2:26][CH2:27][CH2:28][CH3:29])[CH3:16])[CH:18]=[C:19]([OH:24])[C:20]=3[C:3]=2[CH2:4]1

Komponenten

5

Edukt 4

HCID 702EthanolHCID 2581765-(3-Methyloctan-2-yl)benzene-1,3-diolHCID 12716255Ethyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylateHCID 215199881,2-Dihydro-9-hydroxy-2-methyl-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1]benzopyran

Produkt 1

HCID 30438832H-Thieno(2,3-c)(1)benzopyran-9-ol, 1,4-dihydro-7-(1,2-dimethylheptyl)-2,4,4-trimethyl-Ausbeute 81 %

Versuchsvorschrift

To 45 ml. of ethanol is added 8.8 g. of ethyl 5-methyl-3-oxo-tetrahydrothiophene-2-carboxylate and 5 g. of 5-(3-methyl-2-octyl)resorcinol. The mixture is cooled in ice and hydrogen chloride is bubbled in for one-half hour. The mixture is stoppered and let stand at room temperature for 3 days. The reaction mixture is concentrated and dissolved in ether. The ether solution is extracted twice with water and once with aqueous sodium bicarbonate solution. The solution is dried over magnesium sulfate and concentrated. The 1,2-dihydro-9-hydroxy-2-methyl-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1]benzopyran is crystallized from acetonitrile to give 4.65 g., m.p. 146°-149°C. Anal. Calcd. for C21H28O3S (MW = 360.6) C, 69.97; H, 7.83; Found: C, 69.89; H, 8.03. 1,2-Dihydro-9-hydroxy-2-methyl-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1]benzopyran is reacted in a manner similar to that set forth in Example 8 to give 1,2-dihydro-2,4,4-trimethyl-9-hydroxy-7-(3-methyl-2-octyl)-4H-thieno-[2,3-c][1]benzopyran in 81% yield as a yellow oil. Anal. Calcd. for: C23H34O2S (MW = 374.6) C, 73.76; H, 9.15; S, 8.54; Found: C, 74.09; H, 9.68; S, 8.25.

Aufarbeitung

  1. temperatureThe mixture is cooled in ice
  2. customhydrogen chloride is bubbled in for one-half hour
  3. concentrationThe reaction mixture is concentrated
  4. dissolutiondissolved in ether
  5. extractionThe ether solution is extracted twice with water and once with aqueous sodium bicarbonate solution
  6. dry with materialThe solution is dried over magnesium sulfate
  7. concentrationconcentrated
  8. customThe 1,2-dihydro-9-hydroxy-2-methyl-7-(3-methyl-2-octyl)-4-oxo-4H-thieno-[2,3-c][1]benzopyran is crystallized from acetonitrile
  9. customto give 4.65 g

Quellen und Nachweise

ORD-Eintrag
ord-1aeb5b89a64c4ca7976bbee09d06a05f
Quelldatensatz
uspto-grants-1976_06
Patentnummer
US03960871

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