Methanol → HCID 59557735, compound

HRID 425042Notes

Reaction equation

HRID 425042 reaction equation
C([O:4][CH2:5][C:6]1[CH:11]=[CH:10][C:9]([CH2:12][C:13]2[CH:18]=[C:17]([Br:19])[CH:16]=[CH:15][C:14]=2[Cl:20])=[CH:8][CH:7]=1)(=O)C.C1COCC1.CO.O[Li].O>C(OCC)(=O)C.O>[Br:19][C:17]1[CH:16]=[CH:15][C:14]([Cl:20])=[C:13]([CH:18]=1)[CH2:12][C:9]1[CH:10]=[CH:11][C:6]([CH2:5][OH:4])=[CH:7][CH:8]=1

Participants

7

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 59557783HCID 59557783, compound

Product 1

HCID 59557735HCID 59557735, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-(5-bromo-2-chlorobenzyl)benzyl acetate (intermediate AJ) (8.86 g) in 60 mL of a mixture of THF:MeOH:H2O (v/v/v=2:3:1), LiOH.H2O (2.10 g) was added. The solution was stirred at room temperature. After 1 h, H2O (10 mL) and ethyl acetate (100 mL) were added. The aqueous layer was extracted 2× with ethyl acetate. The combined ethyl acetate layers were washed with brine and dried over Na2SO4. The solvent was evaporated under reduced pressure, and the product was purified by column chromatography to obtain pure intermediate AK (6 g).

Workup

  1. extractionThe aqueous layer was extracted 2× with ethyl acetate
  2. washThe combined ethyl acetate layers were washed with brine
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated under reduced pressure
  5. customthe product was purified by column chromatography
  6. customto obtain pure intermediate AK (6 g)

Sources & evidence

ORD record
ord-c1fc6659a0c346719e908427ab79420a
Source dataset
uspto-grants-2012_01
Patent number
US08106021B2

Reaction notes

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