Methanol → HCID 58372800, compound

HRID 656721Notes

Reaction equation

HRID 656721 reaction equation
[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[CH:24]=[O:25])[CH:7]=1)[CH3:2].CO.[BH4-].[Na+]>>[CH2:1]([O:3][C:4](=[O:26])[CH2:5][C:6]1[CH:11]=[CH:10][C:9]([O:12][CH3:13])=[C:8]([O:14][C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][C:16]=2[CH2:24][OH:25])[CH:7]=1)[CH3:2]

Participants

4

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 58288506HCID 58288506, compound

Product 1

HCID 58372800HCID 58372800, compound

Procedure

To [3-(2-formyl-4-nitro-phenoxy)-4-methoxy-phenyl]-acetic acid ethyl ester (1 equivalent methanol was added sodium borohydride (1.2 equivalents), and the reaction was stirred at room temperature for 15 minutes. The mixture was then concentrated and partitioned between EtOAc and H2O. The aqueous layer was separated and extracted with EtOAc, and the combined organic layers were dried over MgSO4, filtered, and concentrated to give the title compound.

Workup

  1. concentrationThe mixture was then concentrated
  2. custompartitioned between EtOAc and H2O
  3. customThe aqueous layer was separated
  4. extractionextracted with EtOAc
  5. dry with materialthe combined organic layers were dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-a29c8cd2f1754c39b4b5f00fa09b38b6
Source dataset
uspto-grants-2011_12
Patent number
US08071807B2

Reaction notes

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