Imidazole → (S)-4-tert-butyldimethylsilyloxy-1-trityloxy-2-butanol
Reaction equation
[C:1]([O:20][CH2:21][C@@H:22]([OH:26])[CH2:23][CH2:24][OH:25])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[Si:32](Cl)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]>CN(C=O)C>[Si:32]([O:25][CH2:24][CH2:23][C@H:22]([OH:26])[CH2:21][O:20][C:1]([C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1)([C:35]([CH3:38])([CH3:37])[CH3:36])([CH3:34])[CH3:33]Participants
Conditions
- Temperature
- 0 °C
Procedure
(S)-1-Trityloxy-2,4-butanediol (1.64 g, 4.7 mmol) and imidazole (0.321 g, 4.715 mmol) were dissolved in DMF (20 ml) and the solution was cooled to 0° C. To the solution was dropped tert-butyldimethylsilyl chloride (0.5 ml, 1.44 mmol, 50% in toluene). After stirring for 1 hour, again to the solution was dropped tert-butyldimethylsilyl chloride (0.5 ml, 1.44 mmol) and the solution was stirred for 1 hour. Further tert-butyldimethylsilyl chloride (0.6 ml, 1.73 mmol) was added to the solution and the solution was stirred over night at room temperature. After dilution with toluene (100 ml), the solution was washed with water (100 ml) twice and saturated brine once, dried on magnesium sulfate, filtered and condensed in vacuo. The residue was subjected to silica gel chromatography to give (S)-4-tert-butyldimethylsilyloxy-1-trityloxy-2-butanol (1.80 g, yield 82.6%).
Workup
- stirringthe solution was stirred for 1 hour
- stirringthe solution was stirred over night at room temperature
- washAfter dilution with toluene (100 ml), the solution was washed with water (100 ml) twice
- dry with materialsaturated brine once, dried on magnesium sulfate
- filtrationfiltered
- customcondensed in vacuo
Sources & evidence
- ORD record
- ord-d3834080934048c7b841f232f72039d1
- Source dataset
- uspto-grants-2003_09
- Patent number
- US06620977B1
Reaction notes
Loading…