Water → 4-Tert-butyl-2-chloromethyl-5-hydroxy-2,3-dihydrobenzofuran

HRID 1376966Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1376966
N1C=CC=CC=1.[C:7]([C:11]1[C:16]2[CH2:17][CH:18]([CH2:20]O)[O:19][C:15]=2[CH:14]=[CH:13][C:12]=1[OH:22])([CH3:10])([CH3:9])[CH3:8].S(Cl)([Cl:25])=O.O>C1C=CC=CC=1>[C:7]([C:11]1[C:16]2[CH2:17][CH:18]([CH2:20][Cl:25])[O:19][C:15]=2[CH:14]=[CH:13][C:12]=1[OH:22])([CH3:10])([CH3:9])[CH3:8]

Komponenten

6

Edukt 4

HCID 962WaterHCID 1049PyridineHCID 24386Thionyl ChlorideHCID 229186574-Tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuran

Produkt 1

HCID 229186814-Tert-butyl-2-chloromethyl-5-hydroxy-2,3-dihydrobenzofuranAusbeute 61,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 241BenzeneLösungsmittel

Versuchsvorschrift

Pyridine (180 mg, 2.2 mmol) was added to a solution of 4-tert-butyl-5-hydroxy-2-hydroxymethyl-2,3-dihydrobenzofuran (430 mg, 1.9 mmol) in benzene (15 ml) and, subsequently, thionyl chloride (310 mg, 2.6 mmol) was added dropwise under ice cooling. After being allowed to warm to room temperature, the mixture was heated under reflux for 24 h. After cooling, water was added and the solution was extracted with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water, then dried over anhydrous magnesium sulfate and concentrated. The concentrate was purified by silica gel chromatography (chloroform) to afford 4-tert-butyl-2-chloromethyl-5-hydroxy-2,3-dihydrobenzofuran [280 mg (yield, 61%)] as a colorless oil.

Aufarbeitung

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 24 h
  3. temperatureAfter cooling
  4. extractionthe solution was extracted with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated
  8. customThe concentrate was purified by silica gel chromatography (chloroform)

Quellen und Nachweise

ORD-Eintrag
ord-226c5ba4f2ca4f6d9677474129b07d54
Quelldatensatz
uspto-grants-1997_09
Patentnummer
US05663373

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