Imidazole → HCID 57723922, compound

HRID 1987665Notes

Reaction equation

HRID 1987665 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 12179941HCID 12179941, compound

Product 1

HCID 57723922HCID 57723922, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C., stirred solution of trans-2-hydroxymethyl-3,6-dihydro-2H-pyran-3-ol (OA 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 The solvent
  3. customwas removed in vacuo
  4. customthe crude product purified by flash chromatography (25-40% EtOAc in hexane)

Sources & evidence

ORD record
ord-308ae2aad3754826a958bda063f51fdc
Source dataset
uspto-grants-2009_06
Patent number
US07550607B2

Reaction notes

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