Water → 6-Hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-8-carbaldehyde

HRID 2103041Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2103041
[CH3:1][C:2]1[C:14]([OH:15])=[C:13]([CH3:16])[CH:12]=[C:11]2[C:3]=1[CH2:4][CH2:5][C:6]1([O:10]2)[CH2:9][CH2:8][CH2:7]1.[CH3:17][O:18]C(Cl)Cl.O>C(Cl)Cl.Cl[Ti](Cl)(Cl)Cl>[OH:15][C:14]1[C:2]([CH3:1])=[C:3]2[C:11](=[C:12]([CH:17]=[O:18])[C:13]=1[CH3:16])[O:10][C:6]1([CH2:7][CH2:8][CH2:9]1)[CH2:5][CH2:4]2

Komponenten

6

Edukt 3

HCID 962WaterHCID 21004Methane, dichloromethoxy-HCID 115502985,7-Dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutan]-6-ol

Produkt 1

HCID 866054876-Hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1'-cyclobutane]-8-carbaldehyde

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 24193Titanium TetrachlorideKatalysatorHCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a cooled solution of 5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutan]-6-ol (1 g) in DCM (20 mL) was added TiCl4 (0.53 mL) which turned the solution a red color. To the solution was added dichloromethyl methyl ether (0.42 mL) and stirred at 0° C. for 30 min and then at room temperature for 30 min. The solution was poured into water and the DCM was separated, dried and evaporated. The residue was purified by silica gel column eluting with 20% ethylacetate in hexane to give 700 mg of 6-hydroxy-5,7-dimethyl-3,4-dihydrospiro[chromene-2,1′-cyclobutane]-8-carbaldehyde as a yellow solid.

Aufarbeitung

  1. waitat room temperature for 30 min
  2. customthe DCM was separated
  3. customdried
  4. customevaporated
  5. customThe residue was purified by silica gel column
  6. washeluting with 20% ethylacetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-067d23ddd9454e42b893dfa94e086972
Quelldatensatz
uspto-grants-2009_08
Patentnummer
US07576094B2

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