Methanol → 2-(2-(Benzyloxy)phenyl)ethanol

HRID 1533256

Reaktionsgleichung

Reaktionsgleichung von HRID 1533256
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][C:16](OC)=[O:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[BH4-].[Na+].CO>O1CCCC1>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[CH2:15][CH2:16][OH:17])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Komponenten

5

Edukt 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 11076055Methyl 2-(2-(benzyloxy)phenyl)acetate

Produkt 1

HCID 5621842-(2-(Benzyloxy)phenyl)ethanolAusbeute 91,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel2×

Reaktionsbedingungen

Temperatur
45 °C

Versuchsvorschrift

To a solution of methyl (2-benzyloxyphenyl)acetate (935 mg) in tetrahydrofuran (9.4 ml) was added sodium borohydride (600 mg) and the suspension was heated to 45° C. A mixture of methanol (3 ml) and tetrahydrofuran (6 ml) was added dropwise to the mixture and the mixture was stirred for 2 hours. The reaction mixture was concentrated under reduced pressure. The residue was dissolved in dichloromethane and quenched by 1 N aqueous hydrochloric acid solution. The organic layer was washed with brine, dried and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)] to afford 2-(2-benzyloxyphenyl)ethanol (764 mg).

Aufarbeitung

  1. additionwas added dropwise to the mixture
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. dissolutionThe residue was dissolved in dichloromethane
  4. customquenched by 1 N aqueous hydrochloric acid solution
  5. washThe organic layer was washed with brine
  6. customdried
  7. customevaporated under reduced pressure
  8. customThe residue was purified by column chromatography on silica gel [eluting with ethyl acetate - n-hexane (1:1)]

Quellen und Nachweise

ORD-Eintrag
ord-8932cc0226684f3299012341a58ba7e7
Quelldatensatz
uspto-grants-2001_03
Patentnummer
US06207686B1

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