Tetrahydrofuran → Methyl 3-(3-hydroxypropyl)-2-methoxy-4-amino-5-chlorobenzoate

HRID 2074007Notes

Reaction equation

HRID 2074007 reaction equation
[CH2:1]([C:4]1[C:5]([O:16][CH3:17])=[C:6]([CH:11]=[C:12]([Cl:15])[C:13]=1[NH2:14])[C:7]([O:9][CH3:10])=[O:8])[CH:2]=[CH2:3].C1C[O:21]CC1>C1COCC1.COCCOCCOC>[OH:21][CH2:3][CH2:2][CH2:1][C:4]1[C:5]([O:16][CH3:17])=[C:6]([CH:11]=[C:12]([Cl:15])[C:13]=1[NH2:14])[C:7]([O:9][CH3:10])=[O:8]

Participants

4

Reactant 2

HCID 8028Tetrahydrofuran2×HCID 14883229Methyl 3-allyl-2-methoxy-4-amino-5-chlorobenzoate

Product 1

HCID 14883230Methyl 3-(3-hydroxypropyl)-2-methoxy-4-amino-5-chlorobenzoate

Reagents, catalysts & solvents 1

HCID 21261944Tetrahydrofuran diglymeSolvent

Conditions

Temperature
20 °C

Procedure

A mixture of a 1M solution of BH3 in THF(8 ml) and the compound of step 3 above (2 g) in THF-diglyme (10 ml/16 ml) is stirred under N2 for 30 minutes at 20° C. Me3NO.2H2O (2.2 g) is added to the mixture and refluxed in a preheated oil bath allowing the THF to evaporate, followed by refluxing the mixture for one hour. The mixture is cooled to 20° C., partitioned between CHCl3 and sat'd aqueous NaHCO3, and stirred for 30 minutes. The organic layer is separated, washed with H2O, dried (MgSO4), evaporated and the residue is chromatographed on silica gel affording the desired product as a solid which is determined to be the correct product by NMR.

Workup

  1. additionMe3NO.2H2O (2.2 g) is added to the mixture
  2. temperaturerefluxed in a preheated oil bath
  3. customto evaporate
  4. temperatureby refluxing the mixture for one hour
  5. custompartitioned between CHCl3
  6. customThe organic layer is separated
  7. washwashed with H2O
  8. dry with materialdried (MgSO4)
  9. customevaporated
  10. customthe residue is chromatographed on silica gel affording the desired product as a solid which

Sources & evidence

ORD record
ord-82378e52f59a4fdf851d1b574f3934db
Source dataset
uspto-grants-1990_04
Patent number
US04920219

Reaction notes

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