4-(2-Bromophenyl)-2-methyl-2-butanol → 2,2-Dimethylchroman

HRID 412747

Reaktionsgleichung

Reaktionsgleichung von HRID 412747
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[CH2:8][CH2:9][C:10]([CH3:13])([OH:12])[CH3:11].CC(C)([O-])C.[Na+]>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].C1(C)C=CC=CC=1>[CH3:11][C:10]1([CH3:13])[CH2:9][CH2:8][C:3]2[C:4](=[CH:5][CH:6]=[CH:7][CH:2]=2)[O:12]1

Komponenten

5

Edukt 2

HCID 152471644-(2-Bromophenyl)-2-methyl-2-butanolHCID 23676156Sodium t-butoxide

Produkt 1

HCID 1369362,2-DimethylchromanAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6505921(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladiumKatalysatorHCID 1140TolueneLösungsmittel

Versuchsvorschrift

A 4 mL vial was charged with 4-(2-bromophenyl)-2-methyl-2-butanol (97 mg, 0.40 mmol), Pd(dba)2 (11.5 mg, 0.02 mmol), Ph5FcP(t-Bu)2 (14.2 mg, 0.02 mmol) and sodium t-butoxide (46 mg, 0.48 mmol). Anhydrous toluene (2 mL) was added into the vial, and the vial was sealed with a cap containing a PTFE septum and removed from the drybox. The reaction mixture was stirred at room temperature for 10 min. The reaction solution was adsorbed onto silica gel and isolated by eluting with 5% ethyl acetate in hexanes to give 60 mg (93%) of 2,2-dimethylchroman as a colorless oil.

Aufarbeitung

  1. customwas sealed with a cap
  2. customremoved from the drybox
  3. customisolated
  4. washby eluting with 5% ethyl acetate in hexanes

Quellen und Nachweise

ORD-Eintrag
ord-c5bdc0ef855d42d0a63794e693c19dc3
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06562989B2

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