Acetone cardice → ethyl 8-(1-hydroxyethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate

HRID 855065

Reaktionsgleichung

Reaktionsgleichung von HRID 855065
[CH:1]([C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)=[O:2].[C:23](=O)=O.CC(C)=O.C[Mg]Br>C1COCC1>[OH:2][CH:1]([C:3]1[CH:4]=[C:5]([CH3:22])[CH:6]=[C:7]2[C:12]=1[O:11][CH:10]([C:13]([F:16])([F:14])[F:15])[C:9]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:8]2)[CH3:23]

Komponenten

5

Edukt 3

HCID 18522661Acetone cardiceHCID 86599485ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylateHCID 178418573HCID 178418573, Verbindung

Produkt 1

HCID 69517760ethyl 8-(1-hydroxyethyl)-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylateAusbeute 54 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

The ethyl 8-formyl-6-methyl-2-(trifluoromethyl)-2H-chromene-3-carboxylate prepared as in Example 605a, Step 1 (1.00 g, 3.18 mmole) was dissolved in anhydrous THF (10 mL) and the solution was cooled to −78° C. (dry ice/acetone). Methylmagnesium bromide (1.16 mL, 3.50 mmole) was added dropwise to the above solution, which was allowed to stir for 2 hours. The reaction was quenched with saturated ammonium chloride (20 mL) and extracted with EtOAc (2×20 mL). The combined extracts were washed with brine (20 mL), dried over MgSO4, filtered and concentrated in vacuo to give a yellow oil. The oil was purified by flash chromatography (silica gel) with 10% MeOH/ CH2Cl2 to give a light yellow oil (0.3g, 54%): GCMS m/z 330.0 (M+). 1H NMR (CDCl3/400 MHz) 7.67 (s, 1H), 7.26 (s, 1H), 6.94 (s, 1H), 5.68 (q, 1H, J=7.0 Hz), 5.11 (m, 1H), 4.30 (m, 2H), 2.28 (s, 3H), 1.47 (m, 3H), 1.34 (m, 3H).

Aufarbeitung

  1. customThe reaction was quenched with saturated ammonium chloride (20 mL)
  2. extractionextracted with EtOAc (2×20 mL)
  3. washThe combined extracts were washed with brine (20 mL)
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customto give a yellow oil
  8. customThe oil was purified by flash chromatography (silica gel) with 10% MeOH/ CH2Cl2

Quellen und Nachweise

ORD-Eintrag
ord-b551388f811e43f0bdb69c57f6ff0da0
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07259266B2

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