Imidazole → 3,5-Bis(methoxymethoxy)benzyl tert-butyldimethylsilyl ether

HRID 1643693Notes

Reaction equation

HRID 1643693 reaction equation
[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH2:15][OH:16])[CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1.N1C=CN=C1.[CH3:22][C:23]([Si:26](Cl)([CH3:28])[CH3:27])([CH3:25])[CH3:24]>C(Cl)Cl>[CH3:1][O:2][CH2:3][O:4][C:5]1[CH:6]=[C:7]([CH:8]=[C:9]([O:11][CH2:12][O:13][CH3:14])[CH:10]=1)[CH2:15][O:16][Si:26]([C:23]([CH3:25])([CH3:24])[CH3:22])([CH3:28])[CH3:27]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 104437513,5-Bis(methoxymethoxy)benzylalcohol

Product 1

HCID 99975163,5-Bis(methoxymethoxy)benzyl tert-butyldimethylsilyl etherYield 97%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of (3,5-bis-methoxymethoxy-phenyl)-methanol (220b) (290 g, 1.27 mol) and imidazole (129 g, 1.9 mol) in CH2Cl2 (1.5 L) was added TBSCl (286 g, 1.9 mol) at 5° C. in several portion was stirred at room temperature overnight. TLC (EtOAc/petroleum ether=1/2) showed that the reaction was complete. The mixture was filtered and the filtrate was washed with water, dried over Na2SO4 and concentrated under high vacuum to give the title compound (320 g, 97%) as a brown oil. 1H NMR (400 MHz, CDCl3): δ 6.68 (d, 2H), 6.57(t, 1H), 5.14 (s, 4H), 4.66 (s, 2H), 3.48 (s, 6H), 0.94 (s, 9H), 0.07 (s, 6H).

Workup

  1. filtrationThe mixture was filtered
  2. washthe filtrate was washed with water
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under high vacuum

Sources & evidence

ORD record
ord-59ce6d2eb24144e89682b294515394be
Source dataset
uspto-grants-2012_02
Patent number
US08119624B2

Reaction notes

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