Methanol → HCID 56640645, compound

HRID 922283Notes

Reaction equation

HRID 922283 reaction equation
O1CCCC1.[CH3:6][O:7]/[N:8]=[C:9](/[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1)\[CH2:10][O:11][C:12]1[CH:34]=[CH:33][C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH2:30][CH2:31][CH3:32])[CH2:25][C:26]([O:28]C)=[O:27])=[CH:20][CH:19]=2)=[CH:14][CH:13]=1.CO.[OH-].[Na+]>O>[CH3:6][O:7]/[N:8]=[C:9](/[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1)\[CH2:10][O:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:16][O:17][C:18]2[CH:23]=[CH:22][C:21]([CH:24]([CH2:30][CH2:31][CH3:32])[CH2:25][C:26]([OH:28])=[O:27])=[CH:20][CH:19]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 87106278HCID 87106278, compound

Product 1

HCID 56640645HCID 56640645, compoundYield 86.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged with 3 mL of tetrahydrofuran. To the stirred solvent were added methyl 3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}hexanoate (0.017 g, 0.03 mmol), methanol (0.5 mL) and sodium hydroxide (0.013 g, 0.32 mmol) in water (0.5 mL). After addition, the reaction mixture was stirred at room temperature 30 minutes. The reaction mixture was concentrated to distill off the solvent; the crude was washed with diethyl ether (5 mL). The salt was dissolved in water (1 mL) and the aqueous layer was acidified with saturated citric acid to solution to make pH 6. The aqueous layer was extracted with ethyl acetate (5 mL). The organic layer was dried over anhydrous Na2SO4 and the solvent was removed under reduced pressure. The crude material was purified by preparative TLC using methanol and chloroform as eluents. The product was obtained as white semi solid (0.012 g, yield: 24.73%). MS (ESI, 120 ev): m/z=462.1 (M+H)+.

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionAfter addition
  3. concentrationThe reaction mixture was concentrated
  4. distillationto distill off the solvent
  5. washthe crude was washed with diethyl ether (5 mL)
  6. dissolutionThe salt was dissolved in water (1 mL)
  7. extractionThe aqueous layer was extracted with ethyl acetate (5 mL)
  8. dry with materialThe organic layer was dried over anhydrous Na2SO4
  9. customthe solvent was removed under reduced pressure
  10. customThe crude material was purified by preparative TLC

Sources & evidence

ORD record
ord-f9bf8e538d8b42478ef1d2e3dd06d084
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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