Isopropanol → HCID 58552948, compound

HRID 85174Notes

Reaction equation

HRID 85174 reaction equation
[NH4+].[Cl-].[CH3:3][C:4]1([CH3:20])[O:8][C@H:7]([CH2:9][O:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([N+:17]([O-])=O)[CH:12]=2)[CH2:6][O:5]1.C(O)(C)C>[Fe].O>[CH3:3][C:4]1([CH3:20])[O:8][C@H:7]([CH2:9][O:10][C:11]2[CH:12]=[C:13]([CH:14]=[CH:15][CH:16]=2)[NH2:17])[CH2:6][O:5]1

Participants

6

Reactant 3

HCID 3776IsopropanolHCID 25517Ammonium ChlorideHCID 58552880(R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane

Product 1

HCID 58552948HCID 58552948, compoundYield 79%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Procedure

Under nitrogen, Fe powder (2.38 g, 42.54 mmol) and NH4Cl (2.38 g, 42.54 mmol) were combined, followed by addition of (R)-2,2-dimethyl-4-((3-nitrophenoxy)methyl)-1,3-dioxolane (132; 1.8 g, 7.09 mmol) and a 4:1 mixture of isopropanol:water (30 mL:10 mL). The reaction mixture was stirred under reflux for 18 h. The crude material was filtered through a pad of Celite and the filtrate was concentrated under reduced pressure. The resulting aqueous layer was extracted with dichloromethane (3×15 mL). The combined organic layers were dried (Na2SO4) and concentrated under reduced pressure to afford (R)-3-((2,2-dimethyl-1,3-dioxolan-4-yl)methoxy)aniline 133 (1.2 g, 79% yield). The material was used in the next step without any further purification.

Workup

  1. temperatureunder reflux for 18 h
  2. filtrationThe crude material was filtered through a pad of Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. extractionThe resulting aqueous layer was extracted with dichloromethane (3×15 mL)
  5. dry with materialThe combined organic layers were dried (Na2SO4)
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6257017f347f41779c809e7323b4ae4f
Source dataset
uspto-grants-2014_09
Patent number
US08846947B2

Reaction notes

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