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

HRID 514635Notes

Reaction equation

HRID 514635 reaction equation
[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:19][OH:20])[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.N1C=CN=C1.[C:26]([Si:30]([C:38]1[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1)([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)Cl)([CH3:29])([CH3:28])[CH3:27].[Cl-].[NH4+]>CN(C)C=O>[CH2:1]([O:8][CH2:9][CH2:10][C:11]1([CH2:19][O:20][Si:30]([C:26]([CH3:29])([CH3:28])[CH3:27])([C:38]2[CH:39]=[CH:40][CH:41]=[CH:42][CH:43]=2)[C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH2:16][O:15][C:14]([CH3:18])([CH3:17])[O:13][CH2:12]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 25517Ammonium ChlorideHCID 94078tert-ButyldiphenylchlorosilaneHCID 903003655-Benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane

Product 1

HCID 903004385-Benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxaneYield 95.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

459 mg (1.64 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-hydroxymethyl-1,3-dioxane was dissolved in 8 mL of dimethylformamide, 197 mg (3.20 mmol equivalents) of imidazole and 0.51 mL (1.92 mmol equivalents) of t-butyldiphenylchlorosilane were added thereto, and the mixture was stirred at room temperature (25° C.) for 22 hours. After completion of the reaction, a saturated aqueous solution of ammonium chloride was added thereto, and the mixture was extracted three times with ethyl acetate. 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 570 mg (1.56 mmol equivalents) of 5-benzyloxyethyl-2,2-dimethyl-5-(t-butyldiphenylsiloxymethyl)-1,3-dioxane.

Workup

  1. customAfter completion of the reaction
  2. extractionthe mixture was extracted three times with ethyl acetate
  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-d607d0918f2649899863c9ff663cee6e
Source dataset
uspto-grants-2015_08
Patent number
US09107964B2

Reaction notes

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