Water → HCID 12816510, compound

HRID 1388740Notes

Reaction equation

HRID 1388740 reaction equation
[C:1]([CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][C:14](=O)[CH3:15])=[CH:9][CH:8]=1)([O:3]C)=O.[O:17]1[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[CH:19]=[C:18]1[CH:26]([OH:29])[CH2:27][NH2:28].O>C1C=CC=CC=1>[OH:3][CH2:1][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([CH2:13][CH:14]([NH:28][CH2:27][CH:26]([C:18]2[O:17][C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[CH:19]=2)[OH:29])[CH3:15])=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 962WaterHCID 128143572-Amino-1-(1-benzofuran-2-yl)ethan-1-olHCID 13851156Methyl 2-(4-(2-oxopropyl)phenoxy)acetate

Product 1

HCID 12816510HCID 12816510, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 1-(4-carbomethoxymethoxyphenyl)-propan-2-one (1 g) and 2-(2-benzofuranyl)-2-hydroxyethanamine (0.8 g) in benzene (80 ml) was boiled under reflux for one hour, with azeotropic removal of water, using a Dean and Stark head. The solution was evaporated, the residue dissolved in methanol (80 ml), cooled in ice, and excess sodium borohydride added. The solution was stirred at ambient temperature for 1 hour, heated under reflux for one hour, the methanol evaporated and the residue partitioned between water and ethyl acetate. The dried organic extract was evaporated to give an oil which was chromatographed on silica gel in 4% methanol/dichloromethane. The resulting oil was treated with ethereal hydrogen chloride to give the title compound as the hydrochloride salt hemi-hydrate, isolated as a 50:50 mixture of diastereoisomers. (mpt 56°-65°) (Ethyl Acetate-Ether).

Workup

  1. customThe solution was evaporated
  2. dissolutionthe residue dissolved in methanol (80 ml)
  3. temperaturecooled in ice
  4. additionexcess sodium borohydride added
  5. temperatureheated
  6. temperatureunder reflux for one hour
  7. customthe methanol evaporated
  8. customthe residue partitioned between water and ethyl acetate
  9. extractionThe dried organic extract
  10. customwas evaporated
  11. customto give an oil which
  12. customwas chromatographed on silica gel in 4% methanol/dichloromethane
  13. additionThe resulting oil was treated with ethereal hydrogen chloride

Sources & evidence

ORD record
ord-8fc7ee799ed1427cbd44f07bd1d72896
Source dataset
uspto-grants-1984_02
Patent number
US04432993

Reaction notes

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