Acetic Acid → HCID 68509730, compound

HRID 2241320Notes

Reaction equation

HRID 2241320 reaction equation
[CH:1](=[N:8]/[C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:16])[CH:10]=1)\[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].[C:19](O)(=[O:21])[CH3:20]>>[CH2:1]([N:8]([C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[C:11]([F:16])[CH:10]=1)[C:19](=[O:21])[CH3:20])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 3

HCID 176Acetic Acid2×HCID 14798Sodium HydroxideHCID 178516248HCID 178516248, compound

Product 1

HCID 68509730HCID 68509730, compoundYield 39%

Procedure

To a stirred solution of (E)-4-(benzylideneamino)-2-fluorophenol (430 mg, 2 mmol) in 1 mL glacial acetic acid at 0° C. under nitrogen was added a solution of trimethylamine/borane complex (160 mg, 2.2 mmol) in 1 mL glacial acetic acid dropwise by syringe. After complete addition, the reaction was allowed to warm to room temperature and was then heated to reflux overnight. 6N NaOH was then added until pH was neutral. The aqueous solution was extracted with ether, and the combined ether extracts were dried (MgSO4), filtered and concentrated. The material was loaded onto a Biotage 40S column with dichloromethane and eluted with 4/1 hexanes/EtOAc to afford the product as a white solid (200 mg, 39% yield).

Workup

  1. additionAfter complete addition
  2. temperaturewas then heated
  3. temperatureto reflux overnight
  4. extractionThe aqueous solution was extracted with ether
  5. dry with materialthe combined ether extracts were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. washeluted with 4/1 hexanes/EtOAc

Sources & evidence

ORD record
ord-6409779ca1b24c7993d2821c1c7843e0
Source dataset
uspto-grants-2010_05
Patent number
US07723330B2

Reaction notes

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