Sulfuric Acid → HCID 57435159, compound

HRID 1366964Notes

Reaction equation

HRID 1366964 reaction equation
[N+:1]([CH:4]([CH3:15])[CH:5]([OH:14])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2].S(=O)(=O)(O)O.[C:21](OC(=O)C)(=[O:23])[CH3:22]>C(Cl)Cl>[N+:1]([CH:4]([CH3:15])[CH:5]([O:14][C:21](=[O:23])[CH3:22])[CH2:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 1118Sulfuric AcidHCID 7918Acetic Anhydride2×HCID 11356253HCID 11356253, compound

Product 1

HCID 57435159HCID 57435159, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Crude 4-Nitro-1-phenyl-pentan-3-ol (179) from above was dissolved in CH2Cl2 (60 mL) and cooled in an ice bath under nitrogen. Concentrated sulfuric acid (0.76 mL, 14.2 mmol) then acetic anhydride (13.83 mL, 146.2 mmol) were added slowly, and the reaction was allowed to warm to room temperature, and was stirred until judged complete by HPLC (3 h, 40 min). (Note: The reaction turned black soon after the addition of the acetic anhydride). The reaction was quenched by pouring slowly into water, then the organic layer was removed, washed with aq. NaHCO3, dried, filtered, and concentrated. The crude product was purified by purified by silica gel chromatography (Combiflash column, 95:5 Hexanes:EtOAc) to achieve pure 180 (21.4447 g, 65.5%, 2 steps). HPLC: 10.45 min.

Workup

  1. temperaturecooled in an ice bath under nitrogen
  2. customuntil judged complete by HPLC (3 h, 40 min)
  3. customThe reaction was quenched
  4. additionby pouring slowly into water
  5. customthe organic layer was removed
  6. washwashed with aq. NaHCO3
  7. customdried
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customThe crude product was purified
  11. customby purified by silica gel chromatography (Combiflash column, 95:5 Hexanes:EtOAc)
  12. custom10.45 min.

Sources & evidence

ORD record
ord-9a0dd0d89f1f4a988db270c226ec4218
Source dataset
uspto-grants-2011_02
Patent number
US07893098B2

Reaction notes

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