Imidazole → HCID 57013861, compound

HRID 1987666Notes

Reaction equation

HRID 1987666 reaction equation
[OH:1][CH2:2][C@H:3]1[C@@H:8]([OH:9])[CH:7]=[CH:6][CH2:5][O:4]1.N1C=CN=C1.[CH3:15][C:16]([Si:19](Cl)([CH3:21])[CH3:20])([CH3:18])[CH3:17]>C(Cl)Cl>[Si:19]([O:1][CH2:2][C@H:3]1[C@@H:8]([OH:9])[CH:7]=[CH:6][CH2:5][O:4]1)([C:16]([CH3:18])([CH3:17])[CH3:15])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 12179942HCID 12179942, compound

Product 1

HCID 57013861HCID 57013861, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C., stirred solution of cis-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (0.4 g, 2.84 mmol) in CH2Cl2 (40 ml) under an Argon atmosphere was added imidazole (0.231 g, 3.4 mmol) followed by TBSCl (0.428 g, 3.4 mmol). The resulting mixture was stirred for 1H at 0° C. The reaction mixture was washed with water (10 ml×2) and brine (10 ml). The organic phase was dried over anhydrous Na2SO4. The solvent was removed in vacuo and the crude product purified by flash chromatography (25-40% EtOAc in hexane).

Workup

  1. washThe reaction mixture was washed with water (10 ml×2) and brine (10 ml)
  2. dry with materialThe organic phase was dried over anhydrous Na2SO4
  3. customThe solvent was removed in vacuo
  4. customthe crude product purified by flash chromatography (25-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-030c271b98e34c04a4693c21b61c32dc
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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