Imidazole → HCID 89676463, compound

HRID 926170Notes

Reaction equation

HRID 926170 reaction equation
[OH:1][CH:2]([C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:17])[CH:12]=2)[C:7]=1[OH:18])[C:3]([O-:5])=[O:4].N1[CH:23]=[CH:22]N=C1.[CH2:24]([Si:26](Cl)([CH2:29][CH3:30])[CH2:27][CH3:28])[CH3:25]>C(Cl)Cl>[CH2:24]([Si:26]([CH2:29][CH3:30])([CH2:27][CH3:28])[O:1][CH:2]([C:6]1[C:15]([CH3:16])=[CH:14][C:13]2[C:8](=[CH:9][CH:10]=[C:11]([CH3:17])[CH:12]=2)[C:7]=1[OH:18])[C:3]([O:5][CH2:22][CH3:23])=[O:4])[CH3:25]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 13819ChlorotriethylsilaneHCID 131735015HCID 131735015, compound

Product 1

HCID 89676463HCID 89676463, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydroxy-2-(1-hydroxy-3,6-dimethylnaphthalen-2-yl)acetate (4.55 g, 16.6 mmol) in DCM (165 mL) at 0° C. was subsequently treated with imidazole (1.53 g, 22.4 mmol) and triethylsilyl chloride (3.2 mL, 19.1 mmol). The cooling bath was removed and the reaction allowed to warm to room temperature over 1.5 hours. Water was added, and the resulting aqueous layer was extracted with DCM. The combined organics were washed with 1M HCl and brine. Following drying over anhydrous MgSO4, concentration in vacuo afforded the desired product that was used without further purification.

Workup

  1. customThe cooling bath was removed
  2. additionWater was added
  3. extractionthe resulting aqueous layer was extracted with DCM
  4. washThe combined organics were washed with 1M HCl and brine
  5. dry with materialFollowing drying over anhydrous MgSO4, concentration in vacuo

Sources & evidence

ORD record
ord-500fbb0898554b8ab93cd24df85985e8
Source dataset
uspto-grants-2016_03
Patent number
US09284323B2

Reaction notes

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