Water → HCID 59259036, compound

HRID 1046371Notes

Reaction equation

HRID 1046371 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]#[CH:13])=[CH:6][C:5]=1[CH:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)[OH:15])([O-])=O.O.C(OCC)(=O)C>C(O)(=O)C.[Fe]>[NH2:1][C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][C:12]#[CH:13])=[CH:6][C:5]=1[C:14]([C:16]1[CH:17]=[CH:18][C:19]([CH:22]2[CH2:23][CH2:24]2)=[CH:20][CH:21]=1)=[O:15]

Participants

6

Reactant 3

HCID 962WaterHCID 8857Ethyl AcetateHCID 59259062HCID 59259062, compound

Product 1

HCID 59259036HCID 59259036, compound

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2.2 g (6.85 mmol) of (2-nitro-5-propargyloxyphenyl)-(4-cyclopropyl-phenyl)-methanol (step C above) in 40 ml glacial acetic acid is heated to 50° C. and treated with 3.06 g (8 equiv.) of iron powder. After 5 h stirring at that temperature the reaction is complete. The green-grey suspension is cooled to rt, diluted by the addition of 500 ml water and 200 ml ethyl acetate and filtered through a pad of Celite. The layers are separated and the organic phase washed with water and sat. bicarbonate solution. The yellow and sticky crude product is purified by chromatography (dichloromethane/MeOH) to yield a viscous yellow oil.

Workup

  1. filtrationfiltered through a pad of Celite
  2. customThe layers are separated
  3. washthe organic phase washed with water and sat. bicarbonate solution
  4. customThe yellow and sticky crude product is purified by chromatography (dichloromethane/MeOH)
  5. customto yield a viscous yellow oil

Sources & evidence

ORD record
ord-ecaf853a94ec4f48becc84660ac4444e
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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