2-Cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl ester → 2-Cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-methanol

HRID 1367635Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1367635
C[O:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][CH:9]([CH:19]3[CH2:21][CH2:20]3)[O:10][C:11]=2[C:12]([O:17][CH3:18])=[C:13]([O:15][CH3:16])[CH:14]=1)=O.COCCO[AlH2-]OCCOC.[Na+]>O1CCCC1.CC(OC)(C)C>[CH:19]1([CH:9]2[CH:8]=[CH:7][C:6]3[C:11](=[C:12]([O:17][CH3:18])[C:13]([O:15][CH3:16])=[CH:14][C:5]=3[CH2:3][OH:2])[O:10]2)[CH2:20][CH2:21]1

Komponenten

5

Edukt 2

HCID 116449742-Cyclopropyl-7,8-dimethoxy-2H-chromene-5-carboxylic acid methyl esterHCID 16684438Red-Al

Produkt 1

HCID 115506842-Cyclopropyl-7,8-dimethoxy-2H-1-benzopyran-5-methanolAusbeute 82,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 15413tert-Butyl methyl etherLösungsmittel

Reaktionsbedingungen

Temperatur
40 °C

Versuchsvorschrift

Methyl ester 2 (2 g, 6.2 mmol) was dissolved in 30 ml tetrahydrofurane and 2.7 ml of a 3.5-M solution of Red-Al (9.4 mmol) was added. The mixture was stirred at 40° C. for 3 hours. The solution was diluted with 100 ml of TBME and slowly quenched by addition of 50 ml of a 30% potassium-tartrate solution. The layers were separated and the organic solution was washed with brine (2 times 30 ml), dried over magnesium sulfate and concentrated. The pure alcohol 4 (1.34 g, 5.1 mmol) was obtained as a white-yellow solid.

Aufarbeitung

  1. customslowly quenched by addition of 50 ml of a 30% potassium-tartrate solution
  2. customThe layers were separated
  3. washthe organic solution was washed with brine (2 times 30 ml)
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated

Quellen und Nachweise

ORD-Eintrag
ord-365dde01fbf14fa9bffb9d6163b257d4
Quelldatensatz
uspto-grants-2011_02
Patentnummer
US07893262B2

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