Sulfuric acid magnesium salt (1:1) → F-15063

HRID 1373997Notes

Reaction equation

HRID 1373997 reaction equation
S([O-])([O-])(=O)=O.[Mg+2].[C:7]1([C:12]2[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=2)[CH:15]=O)[CH2:11][CH2:10][CH2:9][CH:8]=1.[CH3:20][C:21]1([CH3:34])[CH2:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH2:31][CH2:32][NH2:33])[C:23]=2[O:22]1.[BH4-].[K+]>ClCCCl>[CH3:20][C:21]1([CH3:34])[CH2:25][C:24]2[CH:26]=[CH:27][CH:28]=[C:29]([O:30][CH2:31][CH2:32][NH:33][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[C:12]([C:7]4[CH2:11][CH2:10][CH2:9][CH:8]=4)[CH:13]=3)[C:23]=2[O:22]1

Participants

6

Reactant 4

HCID 24083Sulfuric acid magnesium salt (1:1)HCID 4192641Potassium borohydrideHCID 12094928HCID 12094928, compoundHCID 16109477HCID 16109477, compound

Product 1

HCID 10248159F-15063Yield 51.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

1.5 g of magnesium sulfate are added to a solution of 3-cyclopenten-1-ylbenzaldehyde (2a) (0.56 g, 3.26 mmol) and of [2-(2,2-dimethyl-2,3-dihydrobenzofuran-7-yl-oxy)]ethylamine (3a) (0.68 g, 3.26 mmol) in 15 ml of 1,2-dichloroethane and the mixture is heated at 60° C. for 17 hours. The mixture is cooled to room temperature, the solid is filtered and the solvent is evaporated under reduced pressure. The residue is diluted with 15 ml of methanol and then cooled to 0° C. 0.35 g of potassium borohydride (6.52 mmol) is then introduced and the reaction mixture is stirred for 3 hours at 0° C. The mixture is then poured into ice-cold water, extracted with ethyl acetate and washed with a saturated aqueous sodium chloride solution. The combined organic phases are dried over magnesium sulfate, filtered and the solvent is evaporated under reduced pressure. The residue is purified by chromatography on silica gel (methylene chloride/methanol/aqueous ammonia: 98/1.5/0.5). The title product (0.61 g) is isolated in the form of a colorless oil.

Workup

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationthe solid is filtered
  3. customthe solvent is evaporated under reduced pressure
  4. additionThe residue is diluted with 15 ml of methanol
  5. temperaturecooled to 0° C
  6. additionThe mixture is then poured into ice-cold water
  7. extractionextracted with ethyl acetate
  8. washwashed with a saturated aqueous sodium chloride solution
  9. dry with materialThe combined organic phases are dried over magnesium sulfate
  10. filtrationfiltered
  11. customthe solvent is evaporated under reduced pressure
  12. customThe residue is purified by chromatography on silica gel (methylene chloride/methanol/aqueous ammonia: 98/1.5/0.5)

Sources & evidence

ORD record
ord-b74206b81c02401283790deccbea8468
Source dataset
uspto-grants-2007_01
Patent number
US07163957B2

Reaction notes

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