Methanol → HCID 68501367, compound

HRID 888362Notes

Reaction equation

HRID 888362 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[C:11]([C:17]([O:19]C)=[O:18])[CH:10]=1.CO.[OH-].[Na+]>C1COCC1>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[C:13]([CH:15]=[CH2:16])[CH:12]=[C:11]([C:17]([OH:19])=[O:18])[CH:10]=1

Participants

5

Reactant 3

HCID 887MethanolHCID 14798Sodium Hydroxide2×HCID 68502348HCID 68502348, compound

Product 1

HCID 68501367HCID 68501367, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 500 mL flask charged with methyl ester from step C above (20 g, 74 mmol) in THF (250 mL) was added MeOH (100 mL) and aq. 3N NaOH (74 mmol, 25 mL). The mixture was stirred overnight at rt and an additional 15 mL NaOH added. Reaction stirred for 16 h, the pH was then adjusted 4-5 and the mixture extracted repeatedly with EtOAc. The combined organic layers were washed with brine, dried over Na2SO4 and concentrated to dryness to give 18.5 g of product as a white solid.

Workup

  1. customReaction
  2. stirringstirred for 16 h
  3. extractionthe mixture extracted repeatedly with EtOAc
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-bc26d8897c4e4c63875261edba0cee5b
Source dataset
uspto-grants-2012_08
Patent number
US08247401B2

Reaction notes

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