Reaktion #62581

Reaktionsgleichung

10

1-Hexadecyloxy-2-fluoromethyl-3-triphenylmethoxypropan

HBr acetic acid

→

title compound ( 11 )

Ausbeute 88.0%

3-Hexadecyloxy-2-fluoromethyl-1-propanol

Ausbeute 88.0%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   FiltrationThe solution was filtered
2. 2
   workup.ADDITIONthe filtrate was poured into ice water
3. 3
   Sonstigethe mixture was partitioned between methylene chloride and water
4. 4
   WaschenThe aqueous layer was washed with two portions of methylene chloride
5. 5
   Waschenthe organic extracts were washed with aqueous Na2CO3 and water
6. 6
   Trocknendried over Na2SO4
7. 7
   Einengenconcentrated
8. 8
   SonstigeThe residue was chromatographed on silica gel

Vorschrift

A solution of 0.750 g (123 mmol) of 10 in 5 ml glacial acetic acid was cooled to 0°. To this was added 2 ml of HBr-acetic acid and the mixture was stirred at 0° for 45 seconds. The solution was filtered and the filtrate was poured into ice water and the mixture was partitioned between methylene chloride and water. The aqueous layer was washed with two portions of methylene chloride and the organic extracts were washed with aqueous Na2CO3 and water, dried over Na2SO4, and concentrated. The residue was chromatographed on silica gel using hexane-ethyl acetate eluent (9:1, v/v) to afford 0.388 g (88%) of the title compound (11) as a colorless wax, m.p. 34°. NMR (CDCl3, (CH3)4Si); δ0.90 (t, 3H, J=6 Hz), 1.25 (s, br, 26H), 1.59 (m, 2H), 2.10 (s, br, --OH), 2.19 (d of septets, 1H, JH--H)=6 Hz, JH--F =21 Hz), 3.45 (t, 2H, J=6.5 Hz), 3.63 (d, 2H, J=6 Hz), 3.85 (d, 2H, J=6 Hz, CH2OH), 4.64 (d of d, 2H, JH--H =6 Hz, JH-F=47 Hz).

Quelle