Ammonium Chloride → HCID 59259062, compound

HRID 1046370Notes

Reaction equation

HRID 1046370 reaction equation
[Mg].Br[C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH2:10]2)=[CH:5][CH:4]=1.[N+:12]([C:15]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]#[CH:26])=[CH:19][C:16]=1[CH:17]=[O:18])([O-:14])=[O:13].[Cl-].[NH4+]>C1COCC1>[N+:12]([C:15]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][C:25]#[CH:26])=[CH:19][C:16]=1[CH:17]([C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:11][CH2:10]2)=[CH:5][CH:4]=1)[OH:18])([O-:14])=[O:13]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 122213551-Bromo-4-cyclopropylbenzeneHCID 59259087HCID 59259087, compound

Product 1

HCID 59259062HCID 59259062, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A suspension of 407 mg (16.7 mmol) magnesium turnings in 5 ml anhydrous THF is treated with a solution of 1-bromo-4-cyclopropyl-benzene in 20 ml THF at such a rate to maintain gentle reflux. Stirring is continued for another ½ h after complete addition. The resulting Grignard reagent is then slowly added to a solution of 2-nitro-5-propargyloxy-benzaldehyde in 30 ml THF at −75° C. The reaction is kept between −75° C. and −65° C. throughout the addition, followed by slow warming to rt. The mixture is then poured into saturated aqueous ammonium chloride solution and extracted with diethyl ether. Purification of the crude product by flash chromatography (hexane/dichloromethane) yields a yellow brown oil.

Workup

  1. temperatureto maintain gentle reflux
  2. additionafter complete addition
  3. additionThe reaction is kept between −75° C. and −65° C. throughout the addition
  4. extractionextracted with diethyl ether
  5. customPurification of the crude product by flash chromatography (hexane/dichloromethane)
  6. customyields a yellow brown oil

Sources & evidence

ORD record
ord-a4e9c0cd895f447295b7de0b37243b3a
Source dataset
uspto-grants-2013_10
Patent number
US08569317B2

Reaction notes

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