Chloroform → {3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyphenyl}methanol

HRID 1028923

Reaktionsgleichung

Reaktionsgleichung von HRID 1028923
[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH:12]=[O:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[BH4-].[Na+].C(Cl)(Cl)Cl>CO>[Si:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][OH:13])([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:2])[CH3:3]

Komponenten

5

Edukt 3

HCID 6212ChloroformHCID 3595583-((tert-Butyldimethylsilyl)oxy)-4-methoxybenzaldehydeHCID 4311764Sodium borohydride

Produkt 1

HCID 11572549{3-[(Tert-butyldimethylsilyl)oxy]-4-methoxyphenyl}methanolAusbeute 73,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

To a cooled solution of 3-[(tert-Butyldimethylsilyl)oxy]-4-methoxybenzaldehyde 13 (17.5 g, 65.7 mmol) in methanol (100 mL) under nitrogen, sodium borohydride (2.98 g, 78.8 mmol) was added and stirred at room temperature for 30 min. After the reaction was complete as indicated by TLC (chloroform on silica gel plate), ice was added to the reaction mixture and extracted with ethyl acetate. The organic layer was separated, washed with water and dried. Removal of solvent in vacuo yielded on yellow oil 14 (73.5%). 1H NMR: δ 0.18 (s, 6H, 2×CH3), 1.00 (s, 9H, 3×CH3), 1.90 (br s, 1H, OH), 3.82 (s, 3H, OCH3), 4.56 (s, 2H, CH2OH), 6.94 (br s, 3H, Ar—H). Anal. Calcd for C14H24O3Si: C, 62.64, H, 9.01. Found: C, 62.59, H, 9.03.

Aufarbeitung

  1. additionwas added to the reaction mixture
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with water
  5. customdried
  6. customRemoval of solvent in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-733c8dd9dd1245078779f65fc303d88b
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08735620B2

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