Imidazole → HCID 22709782, compound

HRID 1061019Notes

Reaction equation

HRID 1061019 reaction equation
[OH:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=2)[CH2:4]1.N1C=CN=C1.[Si:22](Cl)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23].CO>CN(C)C=O>[Si:22]([O:1][CH2:2][CH:3]1[CH2:12][CH2:11][C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:13]([O:15][CH3:16])=[O:14])[CH:9]=2)[CH2:4]1)([C:25]([CH3:28])([CH3:27])[CH3:26])([CH3:24])[CH3:23]

Participants

6

Reactant 4

HCID 795ImidazoleHCID 887MethanolHCID 28928tert-Butyldimethylsilyl chlorideHCID 13851838Methyl 6-hydroxymethyl-5,6,7,8-tetrahydro-2-naphthalenecarboxylate

Product 1

HCID 22709782HCID 22709782, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In N,N-dimethylformamide (5 ml), (2RS)-2-hydroxymethyl-6-methoxycarbonyl-1,2,3,4-tetrahydronaphthalene (1.71 g) was dissolved, followed by the addition of imidazole (0.81 g) and tert-butyldimethylsilyl chloride (1.81 g) under ice cooling. The resulting mixture was stirred at room temperature for 14 hours. After the addition of methanol, the mixture was concentrated under reduced pressure. The concentrate was diluted with ethyl acetate, washed with water and then dried over anhydrous sodium sulfate. The residue obtained by distilling off the solvent under reduced pressure was purified by chromatography on a silica gel column (hexane:ethyl acetate=50:1), whereby a yellow solid (2.20 g, 85%) was obtained.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. additionThe concentrate was diluted with ethyl acetate
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe residue obtained
  6. distillationby distilling off the solvent under reduced pressure
  7. customwas purified by chromatography on a silica gel column (hexane:ethyl acetate=50:1), whereby a yellow solid (2.20 g, 85%)
  8. customwas obtained

Sources & evidence

ORD record
ord-1b7949180d174d7cb77547329b67fa3e
Source dataset
uspto-grants-2003_02
Patent number
US06525042B1

Reaction notes

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