Acetic Acid → HCID 11646327, compound

HRID 505654Notes

Reaction equation

HRID 505654 reaction equation
[CH2:1]([O:8][CH2:9][C:10]1[C:18]([Br:19])=[C:17]([O:20]COC)[CH:16]=[C:15]([O:24]COC)[C:11]=1[C:12]([OH:14])=[O:13])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:28][Si](C=[N+]=[N-])(C)C.CCCCCC.C(O)(=O)C>CO>[CH3:28][O:14][C:12](=[O:13])[C:11]1[C:15]([OH:24])=[CH:16][C:17]([OH:20])=[C:18]([Br:19])[C:10]=1[CH2:9][O:8][CH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 86587183Trimethylsilyldiazomethane hexaneHCID 866163832-(Benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acid

Product 1

HCID 11646327HCID 11646327, compoundYield 83.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The above-obtained 2-(benzyloxymethyl)-3-bromo-4,6-bis(methoxymethoxy)benzoic acid (16 mg, 0.036 mmol) was dissolved in methanol (2 mL) and the obtained mixture was further added with 2.0 mol/L trimethylsilyldiazomethane-hexane solution (0.30 mL, 0.60 mmol) followed by stirring at a room temperature for 1 hour. After adding acetic acid (0.050 mL) to the reaction mixture, the solvent was evaporated under reduced pressure. The obtained residue was dissolved in ethanol (4 mL) and the obtained solution was added with concentrated hydrochloric acid (0.10 mL) followed by stirring at 60° C. for 1 hour. The reaction mixture was concentrated under reduced pressure and the obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1) to obtain Compound 10 (11 mg, 82%).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. dissolutionThe obtained residue was dissolved in ethanol (4 mL)
  3. additionthe obtained solution was added with concentrated hydrochloric acid (0.10 mL)
  4. stirringby stirring at 60° C. for 1 hour
  5. concentrationThe reaction mixture was concentrated under reduced pressure
  6. customthe obtained residue was purified by preparative thin-layer chromatography (chloroform/methanol=20/1)

Sources & evidence

ORD record
ord-4dea6bc2c52249c9964a3c836c477659
Source dataset
uspto-grants-2010_08
Patent number
US07781485B2

Reaction notes

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