(2S)-6-benzyloxy-1-(4-fluorophenoxy)-2-(methoxyethoxymethyloxy)-hex-4-yne → (2S)-1-(4-fluorophenoxy)-2-(methoxyethoxymethyloxy)-hexan-6-ol
Reaction equation
C([O:8][CH2:9][C:10]#[C:11][CH2:12][C@H:13]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH2:14][O:15][C:16]1[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=1)C1C=CC=CC=1>CO.[Pd]>[F:22][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][C@@H:13]([O:23][CH2:24][O:25][CH2:26][CH2:27][O:28][CH3:29])[CH2:12][CH2:11][CH2:10][CH2:9][OH:8])=[CH:21][CH:20]=1Participants
Procedure
To a solution of (2S)-6-benzyloxy-1-(4-fluorophenoxy)-2-(methoxyethoxymethyloxy)-hex-4-yne (2.2 g, 5.4 mmol) in dry methanol (20 ml) was added 10% Pd/C (250mg) and the mixture stirred under H2 at room temperature for 4 h. The reaction mixture was filtered through celite, washed with excess methanol. Evaporation of the solvent afforded a crude product which was purified by silica gel column using ethyl acetate-light petroleum (2:3) as eluent to give (2S)-1-(4-fluorophenoxy)-2-(methoxyethoxymethyloxy)-hexan-6-ol (1.3 g, 76%) as a colourless liquid. TLC:ethyl acetate-light petroleum (2.3), Rf=0.3. 1H NMR (CDCl3, 200 MHz) δ 1.5-1.7 (m, 6H), 3.35 (s, 3H), 3.5 (t, J=4.8 Hz, 2H), 3.65 (t, J=4.8 Hz, 2H), 3.7-3.8 (m, 2H), 3.85-3.95 (s, 3H), 4.75-4.95 (dd, J=12.6, 6.0 Hz, 2H), 6.75-7.0 (m, 4H).
Workup
- filtrationThe reaction mixture was filtered through celite
- washwashed with excess methanol
- customEvaporation of the solvent
- customafforded a crude product which
- customwas purified by silica gel column
Sources & evidence
- ORD record
- ord-0558656790f147abaa71cd013fca709d
- Source dataset
- uspto-grants-2003_05
- Patent number
- US06566538B1
Reaction notes
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