Ammonium Acetate → HCID 9798357, compound

HRID 2395587Notes

Reaction equation

HRID 2395587 reaction equation
[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[C:5](=O)[CH2:4][CH2:3]1.C([O-])(=O)C.[NH4+].C([BH3-])#[N:33].[Na+]>CO.O>[CH3:1][C:2]1([CH3:26])[C:11]2[CH:10]=[CH:9][C:8]([C:12]#[C:13][C:14]3[CH:24]=[CH:23][C:17]([C:18]([O:20][CH2:21][CH3:22])=[O:19])=[CH:16][CH:15]=3)=[CH:7][C:6]=2[CH:5]([NH2:33])[CH2:4][CH2:3]1

Participants

6

Reactant 3

HCID 517165Ammonium AcetateHCID 3025901Benzoic acid, 4-((5,6,7,8-tetrahydro-5,5-dimethyl-8-oxo-2-naphthalenyl)ethynyl)-, ethyl ester2×HCID 5003444Sodium cyanoborohydride

Product 1

HCID 9798357HCID 9798357, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 962WaterSolvent

Procedure

To a solution of 100 mg (0.3 mmol) of ethyl 4-[(5,6,7,8-tetrahydro-8,8-dimethyl-5-oxonaphth-3-yl)ethynyl]benzoate (Compound 2 ) in 5 ml of MeOH was added 922 mg (12 mmol) of ammonium acetate and then 188 mg (3 mmol) of sodium cyanoborohydride. The reaction mixture was refluxed for 1 hour, stirred at ambient temperature for 12 hours and then diluted with water (10 ml) and extracted with Et20 (3×30 ml). The organic layer was washed with water (5 ml) and brine (5 ml), dried over MgSO4 and concentrated in vacuo to an oil. Recrystallization from EtOAc-hexane yielded the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was refluxed for 1 hour
  2. extractionextracted with Et20 (3×30 ml)
  3. washThe organic layer was washed with water (5 ml) and brine (5 ml)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo to an oil
  6. customRecrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-f1c579a9e26243e4be044a04974d3f1c
Source dataset
uspto-grants-1996_02
Patent number
US05489584

Reaction notes

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