Ethylene Glycol → 5'-bromo-3',4'-dihydro-1'H-spiro[[1,3]-dioxolane-2,2'-naphthalene]

HRID 1423381Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1423381
[CH2:1]1[C:10]2[CH:9]=[CH:8][CH:7]=[C:6](C=O)[C:5]=2[CH2:4][CH2:3][C:2]21[O:16][CH2:15][CH2:14][O:13]2.[Br:17]C1C=CC=C2C=1CCC(=O)C2.C(O)CO.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1C=CC=CC=1.CCOCC>[Br:17][C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:5]=1[CH2:4][CH2:3][C:2]1([O:16][CH2:15][CH2:14][O:13]1)[CH2:1]2

Komponenten

7

Edukt 4

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 40596895-Bromo-2-tetraloneHCID 866887243',4'-Dihydro-1'H-spiro[[1,3]dioxolane-2,2'-naphthalene]-5'-carbaldehyde

Produkt 1

HCID 866887235'-bromo-3',4'-dihydro-1'H-spiro[[1,3]-dioxolane-2,2'-naphthalene]Ausbeute 98 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 241BenzeneLösungsmittelHCID 3283Diethyl EtherLösungsmittel

Versuchsvorschrift

3′,4′-Dihydro-1′H-spiro[[1,3]dioxolane-2,2′-naphthalene]-5′-carbaldehyde, designated as 37 in FIG. 15, was prepared as follows: A solution of 5-bromo-3,4-dihydronaphthalen-2(1H)-one (625 mg, 2.78 mmol), ethylene glycol (0.23 mL, 4.17 mmol), and p-toluenesulfonic acid (5.70 mg, 0.03 mol) in benzene (46 mL) was stirred and heated to reflux for 10 h. The solution was cooled, diluted with ether, and sequentially washed with saturated aqueous sodium bicarbonate solution and water. The organic layer was dried over magnesium sulfate, filtered and concentrated in vacuo. Purification by silica gel column chromatography, using a 2:1 mixture of hexanes and AcOEt as eluant, furnished 5′-bromo-3′,4′-dihydro-1′H-spiro[[1,3]-dioxolane-2,2′-naphthalene](730.4 mg, 98% yield) as a yellow oil. Yield: 65%.

Aufarbeitung

  1. customwas prepared
  2. temperatureheated
  3. temperatureto reflux for 10 h
  4. temperatureThe solution was cooled
  5. washsequentially washed with saturated aqueous sodium bicarbonate solution and water
  6. dry with materialThe organic layer was dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customPurification by silica gel column chromatography
  10. additiona 2:1 mixture of hexanes and AcOEt as eluant

Quellen und Nachweise

ORD-Eintrag
ord-cb4ce1ff52c44fddbe565c998b020cf8
Quelldatensatz
uspto-grants-2015_01
Patentnummer
US08927586B2

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