Ethanol → HCID 58019873, compound

HRID 1632109Notes

Reaction equation

HRID 1632109 reaction equation
C(O)C.[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[CH:16]=[C:15]([CH2:17][C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-])=O)=[CH:20][CH:19]=3)[CH:14]=[CH:13][C:12]=2[O:27][CH3:28])[CH:8]=[CH:9][CH:10]=1>[Fe].O>[Cl:4][C:5]1[CH:6]=[C:7]([C:11]2[C:12]([O:27][CH3:28])=[CH:13][CH:14]=[C:15]([CH2:17][C:18]3[CH:19]=[CH:20][C:21]([NH2:24])=[CH:22][CH:23]=3)[CH:16]=2)[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 2

HCID 702EthanolHCID 58020319HCID 58020319, compound

Product 1

HCID 58019873HCID 58019873, compoundYield 89%

Reagents, catalysts & solvents 2

HCID 23925IronCatalystHCID 962WaterSolvent

Conditions

Temperature
85 °C

Procedure

In a 40 mL vial equipped with a stir bar was placed iron powder (586 mg, 10.5 mmol), ethanol (12 mL) and water (3.8 mL). The mixture was heated to 85° C. in an oil bath and then I-270 (1.05 g, 3.00 mmol) was added and the reaction was continued at 85° C. for 2 hours. The reaction mixture was cooled to room temperature and filtered through Celite. To the filtrate was added water (60 mL) and extractions were performed with ethyl acetate (2×60 mL). The organic portions were combined, washed with brine (60 mL), dried (MgSO4) and concentrated to produce 862 mg of I-271 as a pale orange viscous oil in 89% yield. MS (APCI+): 324.1 (M+1); LC-MS: 97%.

Workup

  1. customIn a 40 mL vial equipped with a stir bar
  2. temperatureThe reaction mixture was cooled to room temperature
  3. filtrationfiltered through Celite
  4. additionTo the filtrate was added
  5. extractionwater (60 mL) and extractions
  6. washwashed with brine (60 mL)
  7. dry with materialdried (MgSO4)
  8. concentrationconcentrated
  9. customto produce 862 mg of I-271 as a pale orange viscous oil in 89% yield

Sources & evidence

ORD record
ord-45877c964b4c447b9f31c968b4edfc5e
Source dataset
uspto-grants-2014_07
Patent number
US08791267B2

Reaction notes

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