Water → (3-(Benzyloxy)cyclobutyl)methanol

HRID 1907314Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1907314
[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([C:13](O)=[O:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.O.C(=O)([O-])O.[Na+]>O1CCCC1>[CH2:1]([O:8][CH:9]1[CH2:12][CH:11]([CH2:13][OH:14])[CH2:10]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Komponenten

5

Edukt 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 128151113-(Benzyloxy)cyclobutane-1-carboxylic acid

Produkt 1

HCID 15221213(3-(Benzyloxy)cyclobutyl)methanolAusbeute 93,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

3-benzyloxy-cyclobutanecarboxylic acid (1.67 g) in dry tetrahydrofuran (100 mL) was treated with borane-dimethylsulfide complex (1.3 mL) at 50° C. for 16 hours. Water (4 mL) and saturated sodium hydrogen carbonate (3 mL) were added and the mixture was extracted with ethyl acetate. The organic extracts were washed with brine, dried over sodium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography on silica gel, eluting with ethyl acetate in cyclohexane (0 to 1:1 by volume) to give the title compound (1.46 g). 1H NMR (400 MHz, CHCl3-d): δ 7.29 (d, 5H), 4.36 (d, 2H), 4.08 (t, 1H), 3.91-3.82 (m, 1H), 3.53 (t, 2H), 2.39-2.30 (m, 1H), 2.33-2.22 (m, 1H), 2.10-2.02 (m, 2H), 1.72-1.63 (m, 1H).

Aufarbeitung

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel
  6. washeluting with ethyl acetate in cyclohexane (0 to 1:1 by volume)

Quellen und Nachweise

ORD-Eintrag
ord-18d5dd9a04a74c2fb14ab953e8312fc9
Quelldatensatz
uspto-grants-2013_12
Patentnummer
US08598154B2

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