Benzyl Bromide → (1-((Benzyloxy)methyl)cyclobutyl)methanol

HRID 1180763Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1180763
[OH:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1.O1CCCC1.[H-].[Na+].[CH2:16](Br)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C)C=O>[CH2:16]([O:1][CH2:2][C:3]1([CH2:7][OH:8])[CH2:6][CH2:5][CH2:4]1)[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

6

Edukt 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 24758Sodium hydrideHCID 4498243Cyclobutane-1,1-diyldimethanol

Produkt 1

HCID 11458402(1-((Benzyloxy)methyl)cyclobutyl)methanolAusbeute 86 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To a solution of 8.0 g (69 mmol) of [1-(hydroxymethyl)cyclobutyl]methanol in 120 ml of a 1:1 mixture of tetrahydrofuran:N,N-dimethylformamide was added 3.30 g (69 mmol) of a 60% dispersion of sodium hydride in oil and the contents stirred for 30 min. 8.6 mL (72.4 mmol) of benzyl bromide was then added and the contents stirred for 2 h. The reaction was quenched with aqueous ammonium chloride followed by the addition of diethyl ether. The organic phase was isolated, dried using magnesium sulfate, and concentrated under vacuum to afford the crude product which was purified by silica gel chromatography using ethyl acetate:hexane (3:7) as the eluent to afford 12.0 g (86%) of {1-[(benzyloxy)methyl]cyclobutyl}methanol as a colorless oil. 1H NMR (300 MHz, CDCl3) δ 7.33-7.25 (m, 5H), 4.49 (s, 2H), 3.66 (d, J=6 Hz, 2H), 3.52 (s, 2H), 2.53 (t, J=6 Hz, 1H), 1.91-1.73 (m, 6H). GC-MS m/z 207 (M+H).

Aufarbeitung

  1. stirringthe contents stirred for 2 h
  2. customThe reaction was quenched with aqueous ammonium chloride
  3. additionfollowed by the addition of diethyl ether
  4. customThe organic phase was isolated
  5. customdried
  6. concentrationconcentrated under vacuum
  7. customto afford the crude product which
  8. customwas purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-1e1c4f77ea8740618f623f68238b27c9
Quelldatensatz
uspto-grants-2007_10
Patentnummer
US07282512B2

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