Imidazole → HCID 54414387, compound

HRID 439576Notes

Reaction equation

HRID 439576 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[CH2:9][C@@H:10]([OH:13])[CH2:11][OH:12].N1C=CN=C1.[Si:19](Cl)([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20].O>CN(C)C=O>[O:12]([CH2:11][C@H:10]([OH:13])[CH2:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])[Si:19]([C:22]([CH3:25])([CH3:24])[CH3:23])([CH3:21])[CH3:20]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 962WaterHCID 28928tert-Butyldimethylsilyl chlorideHCID 53761479HCID 53761479, compound

Product 1

HCID 54414387HCID 54414387, compoundYield 84.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Under ice-cooling, to a solution of (R)-3-(2-methoxyphenyl)propane-1,2-diol (1.62 g) and imidazole (0.92 g)in dimethylformamide was added t-butyldimethylsilyl chloride (1.36 g),and stirred for 15minutes successively. The reaction solutionwas poured into water, extracted with ethyl acetate, and dried oversodium sulfate. After the solvent was evaporated in vacuo, thegained crude product was purified by silica gel columnchromatography, and it was eluted with a mixed solvent of hexaneand ethyl acetate (7:1, v/v). The fractions containing the desiredproduct were combined and evaporated in vacuo to obtain (R)-1-t-butyldimethylsiloxy-3-(2-methoxyphenyl)-2-propanol(2.22 g).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried oversodium sulfate
  3. customAfter the solvent was evaporated in vacuo
  4. customthegained crude product was purified by silica gel columnchromatography, and it
  5. washwas eluted with a mixed solvent of hexaneand ethyl acetate (7:1
  6. additionThe fractions containing the desiredproduct
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-77a14b8280eb4b0498caef3b59bf3825
Source dataset
uspto-grants-1996_05
Patent number
US05514773

Reaction notes

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