Reaktion #91359

Reaktionsgleichung

DIAD

6-Hydroxy-1-tetralone

3,3,3-trifluoro-1-propanol

triphenylphosphine

→

title compound

Ausbeute 53.0%

6-(3,3,3-trifluoropropoxy)-3,4-dihydronaphthalen-1(2H)-one

Ausbeute 53.0%

Lösungsmittel

EtOAc

THF

Reaktionsbedingungen

Aufarbeitung

1. 1
   Waschenwashed with brine
2. 2
   TrocknenOrganics were dried (MgSO4)
3. 3
   Einengenconcentrated
4. 4
   SonstigePurification by silica gel chromatography (10-50% EtOAc/hexanes)

Vorschrift

6-Hydroxy-1-tetralone (3.5 g, 21.6 mmol), 3,3,3-trifluoro-1-propanol (4.93 g, 43.2 mmol) and triphenylphosphine (11.3 g, 43.2 mmol) were combined in THF (80 mL). DIAD (8.7 g, 43.2 mmol) was added, and the reaction stirred overnight at rt. The solution was diluted with EtOAc (100 mL) and washed with brine. Organics were dried (MgSO4) and concentrated. Purification by silica gel chromatography (10-50% EtOAc/hexanes) gave 2.93 g (53%) of the title compound as a clear oil. 1H NMR (400 MHz, DMSO-d6): δ 8.02 (d, 1H, J=8.7 Hz), 6.82 (dd, 1H, J=8.7, 2.5 Hz), 6.71 (d, 1H, J=2.4 Hz), 4.25 (t, 2H, J=6.6 Hz), 2.93 (t, 2H, J=6.1 Hz), 2.59-2.71 (m, 4H), 2.08-2.16 (m, 2H). [M+H] calc'd for C13H13F3O2, 259; found 259.

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