Imidazole → (1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

HRID 1672380

Reaction equation

HRID 1672380 reaction equation
[OH:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1.C(N(CC)CC)C.N1C=CN=C1.[Si:20](Cl)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]>C(Cl)Cl>[Si:20]([O:1][CH2:2][C:3]1([CH2:6][OH:7])[CH2:5][CH2:4]1)([C:23]([CH3:26])([CH3:25])[CH3:24])([CH3:22])[CH3:21]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 8471TriethylamineHCID 28928tert-Butyldimethylsilyl chlorideHCID 41014371,1-Bis(hydroxymethyl)cyclopropane

Product 1

HCID 59000904(1-(((tert-Butyldimethylsilyl)oxy)methyl)cyclopropyl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
0 °C

Procedure

1,1-Bis(hydroxymethyl)cyclopropane (1.0 g, 0.0098 mol), triethylamine (TEA) (2.0 mL, 0.015 mol), and 1H-imidazole (0.13 g, 0.0020 mol) were dissolved in anhydrous DCM (15 mL) and the solution was cooled to 0° C. A solution of tert-butyldimethylsilyl chloride (1.55 g, 0.0103 mol) in DCM (5 mL) was added drop-wise and the resulting mixture was allowed to warm to RT and stirred overnight. The reaction was quenched with saturated aqueous NaHCO3 and extracted with DCM (3×). The organic extract was dried (magnesium sulfate), filtered, and concentrated in vacuo. The crude product was identified by 1H NMR and used in the next step without further purification.

Workup

  1. temperatureto warm to RT
  2. customThe reaction was quenched with saturated aqueous NaHCO3
  3. extractionextracted with DCM (3×)
  4. extractionThe organic extract
  5. dry with materialwas dried (magnesium sulfate)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customused in the next step without further purification

Sources & evidence

ORD record
ord-6d2e0e14f7764fbca3d2d7096d880b54
Source dataset
uspto-grants-2011_08
Patent number
US07998959B2

Linked notes

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