Reaktionsgleichung
S(C)C.[CH2:4]([O:11][CH2:12][CH:13]1[CH2:18][CH2:17][CH:16]=[CH:15][O:14]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.C1C[O:22]CC1>>[CH2:4]([O:11][CH2:12][CH:13]1[O:14][CH2:15][CH:16]([OH:22])[CH2:17][CH2:18]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1Komponenten
4
Versuchsvorschrift
BH3.SMe2 (17 mL, 1 M in THF) was added slowly to a stirred solution of 2-(benzyloxymethyl)-3,4-dihydro-2H-pyran (2.87 g, 14.06 mmol) (13) in THF (100 mL) at −78° C. The resulting mixture was allowed to warm to room temperature overnight. The mixture was quenched by the slow addition of 1M NaOH (50 mL) at 0° C. followed by H2O2 (13 mL, 30% in water). The resulting mixture was stirred for 2 hours at room temperature. After aqueous work up the residue was purified on silica gel using EtOAc and hexane to give 6-(benzyloxymethyl)tetrahydro-2H-pyran-3-ol (14).
Aufarbeitung
- customThe mixture was quenched by the slow addition of 1M NaOH (50 mL) at 0° C.
- customAfter aqueous work up the residue was purified on silica gel
Quellen und Nachweise
- ORD-Eintrag
- ord-a64bde3197bf4f988a8575630b34b83c
- Quelldatensatz
- uspto-grants-2013_10
- Patentnummer
- US08569283B2
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