Hydrochloric Acid → HCID 68500658, compound

HRID 1176313Notes

Reaction equation

HRID 1176313 reaction equation
[C:1]([NH:4][CH2:5][CH2:6][C:7]1[C:15]2[O:14][C:13]([C:16](OC)=[O:17])=[CH:12][C:11]=2[CH:10]=[CH:9][CH:8]=1)(=[O:3])[CH3:2].[BH4-].[Li+].Cl>O1CCCC1>[OH:17][CH2:16][C:13]1[O:14][C:15]2[C:7]([CH2:6][CH2:5][NH:4][C:1](=[O:3])[CH3:2])=[CH:8][CH:9]=[CH:10][C:11]=2[CH:12]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4148881Lithium borohydrideHCID 68497272HCID 68497272, compound

Product 1

HCID 68500658HCID 68500658, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 1.41 g of methyl 7-(2-acetylaminoethyl)benzofuran-2-carboxylate in 40 ml of tetrahydrofuran is admixed at 0° C. with 0.30 g of lithium borohydride. The reaction mixture is stirred at room temperature over 4 hours and then admixed slowly with 20 ml of 2N HCl. The mixture is concentrated by evaporation. The residue is taken up in methanol (2×) and once more concentrated by evaporation. The title compound is obtained as an orange oil from the residue by means of flash chromatography (SiO2 60F). Rf=0.47 (9:1 dichloromethane-methanol); Rt=2.67.

Workup

  1. concentrationThe mixture is concentrated by evaporation
  2. concentrationonce more concentrated by evaporation

Sources & evidence

ORD record
ord-8357d5ca689d4687b92f59cf2f8e71b7
Source dataset
uspto-grants-2010_11
Patent number
US07842688B2

Reaction notes

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