Ethanol → HCID 15572606, compound

HRID 903949Notes

Reaction equation

HRID 903949 reaction equation
[OH:1][CH:2]([CH:5]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:3]#[N:4].B#B.C(O)C>C1COCC1>[OH:1][CH:2]([CH:5]([O:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[O:13][CH3:14])[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[Cl:21])[CH2:3][NH2:4]

Participants

5

Reactant 3

HCID 702EthanolHCID 6328200DiboronHCID 15572605HCID 15572605, compound

Product 1

HCID 15572606HCID 15572606, compoundYield 78.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Under an atmosphere of nitrogen to 15.7 g of 2-hydroxy-3-(2-chlorophenyl)-3-(2-methoxy-phenoxy)-propionitrile in 110 ml of anhydrous THF there was added at 15° C. 46.2 ml of a 1.35 M solution of diborane in tetrahydrofuran. Stirring was continued at room temperature for 16 hours. A small quantity of ethanol was added and the whole was evaporated to dryness. The residue was dissolved in ethyl ether, extracted with 3% HCl, made alkaline with 20% NaOH, re-extracted with ethyl ether. After washing with water, drying over Na2SO4, filtration and evaporation to dryness, there was obtained 12.45 g of 2-hydroxy-3-(2-methoxy-phenoxy)-3-(2-chlorophenyl)-propylamine. Yield 78%.

Workup

  1. customthe whole was evaporated to dryness
  2. dissolutionThe residue was dissolved in ethyl ether
  3. extractionextracted with 3% HCl
  4. extractionre-extracted with ethyl ether
  5. washAfter washing with water
  6. dry with materialdrying over Na2SO4, filtration and evaporation to dryness

Sources & evidence

ORD record
ord-1dc37e417a304e8fac6a699fbcbb9fb7
Source dataset
uspto-grants-1980_10
Patent number
US04229449

Reaction notes

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