Acetic Anhydride → HCID 71534205, compound

HRID 541489Notes

Reaction equation

HRID 541489 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7](=[O:26])[CH2:8][CH2:9][CH:10]2[CH2:13][CH2:14][N:15]2[C:23](=[O:24])[C:22]3C(=CC=CC=3)C2=O)=[CH:5][CH:4]=1.[BH4-].[Na+].[OH-].[Na+].CN(C1C=CC=CN=1)C.[C:40](OC(=O)C)(=[O:42])[CH3:41].C(=O)([O-])O.[Na+]>C(O)(C)C.O.ClCCl.CC(C)=O>[C:40]([O:26][CH:7]1[C:6]2[C:11](=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[CH:10]([CH2:13][CH2:14][NH:15][C:23](=[O:24])[CH3:22])[CH2:9][CH2:8]1)(=[O:42])[CH3:41]

Participants

11

Reactant 6

HCID 7918Acetic AnhydrideHCID 14798Sodium HydroxideHCID 218852-DimethylaminopyridineHCID 516892Sodium BicarbonateHCID 4311764Sodium borohydrideHCID 68283851HCID 68283851, compound

Product 1

HCID 71534205HCID 71534205, compoundYield 79%

Reagents, catalysts & solvents 4

HCID 180AcetoneSolventHCID 962WaterSolvent2×HCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of the tetralone obtained in Step C (350 mg, 1.0 mmol) in isopropanol (10 mL) at ambient temperature there is added sodium borohydride (190 mg, 5.0 mmol). The mixture is stirred at reflux overnight and then a solution of sodium hydroxide (80 mg, 2.0 mmol) in water (2.0 mL) is added dropwise. The mixture is maintained under reflux for 30 minutes, and then acetone (1.5 mL) is added. After 10 minutes, the mixture is cooled to ambient temperature before being concentrated under reduced pressure. The oil thereby obtained is dissolved in dichloromethane (10 mL). Dimethylaminopyridine (270 mg, 2.2 mmol) is then added, followed by acetic anhydride (210 μL, 2.2 mmol) dropwise. The solution is stirred at ambient temperature for 1 hour and then water is added. The pH of the solution is adjusted to from 8 to 9 by adding saturated sodium hydrogen carbonate solution. The aqueous phase is extracted with dichloromethane and the organic phases are washed with saturated NaCl solution, dried over magnesium sulphate, filtered and evaporated. The title compound is obtained after purification by flash column chromatography (ethyl acetate-petroleum ether: 90-10, then ethyl acetate-methanol: 90-10) in the form of an oil in a yield of 79%.

Workup

  1. temperatureat reflux overnight
  2. temperatureThe mixture is maintained
  3. temperatureunder reflux for 30 minutes
  4. concentrationbefore being concentrated under reduced pressure
  5. customThe oil thereby obtained
  6. stirringThe solution is stirred at ambient temperature for 1 hour
  7. extractionThe aqueous phase is extracted with dichloromethane
  8. washthe organic phases are washed with saturated NaCl solution
  9. dry with materialdried over magnesium sulphate
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-fde9dc204d45434faaa53d6ff7393760
Source dataset
uspto-grants-2014_10
Patent number
US08871975B2

Reaction notes

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