Imidazole → 5-Bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane

HRID 514622Notes

Reaction equation

HRID 514622 reaction equation
[Br:1][CH2:2][C:3]1([CH2:11][OH:12])[CH2:8][O:7][C:6]([CH3:10])([CH3:9])[O:5][CH2:4]1.N1C=CN=C1.[Cl-].[C:19]([SiH:23]([C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1)[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([CH3:22])([CH3:21])[CH3:20].[Cl-].[NH4+]>CN(C)C=O>[Br:1][CH2:2][C:3]1([CH2:11][O:12][Si:23]([C:19]([CH3:22])([CH3:21])[CH3:20])([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH2:4][O:5][C:6]([CH3:9])([CH3:10])[O:7][CH2:8]1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 581652605-Bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxaneHCID 131727113Tert-butyldiphenyl silane chloride

Product 1

HCID 903003725-Bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxaneYield 77.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

1.1 g (4.6 mmol equivalents) of 5-bromomethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was dissolved in 23 mL of dimethylformamide, 626 mg (9.2 mmol equivalents) of imidazole and 1.43 mL (5.5 mmol equivalents) of t-butyldiphenylsilane chloride were added thereto, and the mixture was stirred at room temperature (25° C.) for 5 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added dropwise, and the mixture was extracted with ethyl acetate three times. The combined ethyl acetate layers were washed with water and brine, then dried with anhydrous magnesium sulfate, and subsequently concentrated under vacuum. The obtained crude product was purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1) to give 1.70 g (3.56 mmol equivalents) of 5-bromomethyl-5-(t-butyldiphenylsiloxymethyl)-2,2-dimethyl-1,3-dioxane.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted with ethyl acetate three times
  3. washThe combined ethyl acetate layers were washed with water and brine
  4. dry with materialdried with anhydrous magnesium sulfate
  5. concentrationsubsequently concentrated under vacuum
  6. customThe obtained crude product
  7. customwas purified by silica gel column chromatography (eluent: hexane/ethyl acetate (v/v)=20/1)

Sources & evidence

ORD record
ord-a09efa332071447b9e3dec60cac1cd05
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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