Imidazole → (R)-1-t-Butyldimethylsilyloxy-3-hydroxytetradecane

HRID 234862Notes

Reaction equation

HRID 234862 reaction equation
[OH:1][C@H:2]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH2:3][CH2:4][OH:5].N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]>CN(C)C=O.C(OCC)(=O)C>[Si:22]([O:5][CH2:4][CH2:3][C@H:2]([OH:1])[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

6

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 11791041HCID 11791041, compound

Product 1

HCID 54036929(R)-1-t-Butyldimethylsilyloxy-3-hydroxytetradecaneYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of diol compound 9 (2.28 g, 10 mmol) in N,N-dimethyl formamide (50 mL) at 0° C. was added sequentially imidazole (1.63 g, 24 mmol), and t-butyldimethylsilyl chloride (1.65 g, 11 mmol), and the reaction mixture was stirred for 2 h. After completion of the reaction (TLC). The mixture was diluted with ethyl acetate (200 mL), washed with water (2×50 mL), dried and concentrated to give a colorless oil, which after purification by flash chromatography, afforded the pure monosilyl compound 10 as an oil (Rf 0.71, silica, ethyl acetate and hexane, 1:10, 2.80 g, 84%).

Workup

  1. customAfter completion of the reaction (TLC)
  2. washwashed with water (2×50 mL)
  3. customdried
  4. concentrationconcentrated
  5. customto give a colorless oil, which
  6. customafter purification by flash chromatography

Sources & evidence

ORD record
ord-8bb3658eee134b3a8e85fbc09c9cea51
Source dataset
uspto-grants-1997_01
Patent number
US05597573

Reaction notes

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