Sodium borohydride → methyl 3-hydroxy-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoate

HRID 922326Notes

Reaction equation

HRID 922326 reaction equation
[CH3:1][O:2]/[N:3]=[C:4](/[C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1)\[CH2:5][O:6][C:7]1[CH:27]=[CH:26][C:10]([CH2:11][O:12][C:13]2[CH:18]=[CH:17][C:16]([C:19](=[O:25])[CH2:20][C:21]([O:23][CH3:24])=[O:22])=[CH:15][CH:14]=2)=[CH:9][CH:8]=1.[BH4-].[Na+]>CO>[OH:25][CH:19]([C:16]1[CH:17]=[CH:18][C:13]([O:12][CH2:11][C:10]2[CH:26]=[CH:27][C:7]([O:6][CH2:5]/[C:4](=[N:3]\[O:2][CH3:1])/[C:28]3[CH:29]=[CH:30][CH:31]=[CH:32][CH:33]=3)=[CH:8][CH:9]=2)=[CH:14][CH:15]=1)[CH2:20][C:21]([O:23][CH3:24])=[O:22]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 87106340methyl 3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]-3-oxopropanoate

Product 1

HCID 87106283methyl 3-hydroxy-3-[4-[[4-[(2Z)-2-methoxyimino-2-phenylethoxy]phenyl]methoxy]phenyl]propanoateYield 50%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a 25 mL RB flask fitted with magnetic stirrer was charged 4 mL of MeOH to the stirred solvent was added methyl 3-{4-[(4-{[(2Z)-2-(methoxyimino)-2-phenylethyl]oxy}benzyl)oxy]phenyl}-3-oxopropanoate (0.08 g, 0.178 mmol) and Sodium borohydride (0.008 g, 1.21 mmol) was added 0° C. Then it was stirred at RT for 6 h, after completion of the reaction (reaction monitored by TLC), reaction mass quenched with Ice water and concentrated the reaction mixture and extracted with ethyl acetate. The organic layer washed with brine and dried by anhydrous Na2SO4 and evaporated to dryness, and the resulting crude compound was purified by column chromatography on silica gel using petroleum ether and ethyl acetate as eluent (0.04 g, Yield: 50%) 1H NMR (300 MHz, DMSO-d6): δ 7.62-7.65 (m, 2H), 7.32-7.40 (m, 5H), 7.23-7.26 (d, 2H), 6.90-6.93 (m, 4H), 5.36-5.38 (d, 1H) 5.22 (s, 2H), 4.92 (s, 2H), 4.85-4.89 (t, 1H), 4.04 (s, 3), 3.57 (s, 3H), 2.57-2.59 (d, 2H)

Workup

  1. customTo a 25 mL RB flask fitted with magnetic stirrer
  2. additionwas added 0° C
  3. customafter completion of the reaction (reaction monitored by TLC), reaction mass
  4. customquenched with Ice water
  5. concentrationconcentrated the reaction mixture
  6. extractionextracted with ethyl acetate
  7. washThe organic layer washed with brine
  8. dry with materialdried by anhydrous Na2SO4
  9. customevaporated to dryness
  10. customthe resulting crude compound was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-78abe7d24384484ea92f806579b9d1cc
Source dataset
uspto-grants-2016_03
Patent number
US09278915B2

Reaction notes

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