Acetic Acid → HCID 89581083, Verbindung

HRID 1500960

Reaktionsgleichung

Reaktionsgleichung von HRID 1500960
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:10])[CH3:9])=[CH:4][C:3]=1[CH3:11].B1(C)OC(C2C=CC=CC=2)(C2C=CC=CC=2)[C@H]2N1CCC2.CSC.B.C(O)(=O)C>ClCCl>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]([OH:10])[CH3:9])=[CH:4][C:3]=1[CH3:11]

Komponenten

6

Edukt 4

HCID 176Acetic AcidHCID 3471241-(4-Bromo-3-methylphenyl)ethanoneHCID 2734713(3aS)-1-methyl-3,3-diphenyl-hexahydropyrrolo(1,2-c)(1,3,2)oxazaboroleHCID 12423031(Dimethyl sulfide)trihydroboron

Produkt 1

HCID 89581083HCID 89581083, VerbindungAusbeute 71,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

A mixture of 1-(4-bromo-3-methylphenyl)ethanone (27.3 g, 128 mmol) and (S)-2-Methyl-CBS-oxazaborolidine (3.6 g, 12.8 mmol) in dichloromethane (500 mL) was added dimethylsulfide-borane (64 mL, 2M in tetrahydrofuran) dropwise at −20° C. and maintained at the same temperature for 2 hours. Acetic acid (15 mL) was added to quench the reaction. The resultant mixture was concentrated to give a residue. Then the mixture was concentrated to give a residue. The residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1) to give (R)-1-(4-bromo-3-methylphenyl)ethanol (19.6 g, 71%)

Aufarbeitung

  1. temperaturemaintained at the same temperature for 2 hours
  2. customto quench
  3. customthe reaction
  4. concentrationThe resultant mixture was concentrated
  5. customto give a residue
  6. concentrationThen the mixture was concentrated
  7. customto give a residue
  8. customThe residue was purified by column chromatography (silica gel, petroleum ether/ethyl acetate=3:1)

Quellen und Nachweise

ORD-Eintrag
ord-f0b0a3d12a694102bdb04c45ce894a95
Quelldatensatz
uspto-grants-2015_12
Patentnummer
US09206128B2

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