Imidazole → (R)-3-[(1,1-dimethylethyl)dimethylsilyloxy]tetradecanoic acid
Reaction equation
[OH:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([OH:6])=[O:5].N1C=CN=C1.[Si:23](Cl)([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24].ClCCl>CO>[Si:23]([O:1][C@H:2]([CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17])[CH2:3][C:4]([OH:6])=[O:5])([C:26]([CH3:29])([CH3:28])[CH3:27])([CH3:25])[CH3:24]Participants
Procedure
A mixture of 2.44 g (R)-3-hydroxytetradecanoic acid (0.01 mole), 2.72 g imidazole (0.04 mole), 3.03 g t-butyldimethylsilyl chloride (0.02 mole), and 50 mL dichloromethane was stirred at room temperature for 22 hours. 5 mL Methanol was added and the resultant mixture was stirred at room temperature for 15 minutes after which it was concentrated to dryness on a rotary evaporator (ca. 100 mm Hg, 35° C.). The residue was chromatographed on a 1" column slurry packed with silica gel in chloroform. The product was eluted with 5% methanol in chloroform. The chromatography was monitored by TLC (silica gel, 5% methanol in chloroform, phosphomolybdic acid visualization, product Rf ca. 0.6) and fractions containing only product were pooled and concentrated on a rotary evaporator (ca. 1 mm Hg, 30° C.) to a clear oil (2.84 g, 79% yield).
Workup
- concentrationwas concentrated to dryness on a rotary evaporator (ca. 100 mm Hg, 35° C.)
- customThe residue was chromatographed on a 1" column slurry
- washThe product was eluted with 5% methanol in chloroform
- additioncontaining only product
Sources & evidence
- ORD record
- ord-474d790723604240a271e6548c17a143
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05420305
Reaction notes
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