Triethylamine → HCID 18945167, compound

HRID 399825Notes

Reaction equation

HRID 399825 reaction equation
[N:1]1([C:6]2[CH:7]=[C:8]([C:15]([O:17][CH3:18])=[O:16])[CH:9]=[C:10]([CH:14]=2)[C:11](O)=[O:12])[CH:5]=[CH:4][CH:3]=[CH:2]1.C(N(CC)CC)C.ClC(OCC(C)C)=O>O1CCCC1>[OH:12][CH2:11][C:10]1[CH:9]=[C:8]([CH:7]=[C:6]([N:1]2[CH:5]=[CH:4][CH:3]=[CH:2]2)[CH:14]=1)[C:15]([O:17][CH3:18])=[O:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 62365Isobutyl chloroformateHCID 18945316HCID 18945316, compound

Product 1

HCID 18945167HCID 18945167, compoundYield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-(pyrrol-1-yl)-3-methoxycarbonylbenzoic acid (9.37 g) in tetrahydrofuran (100 ml) was added triethylamine (6.4 ml) followed by slow addition of isobutyl chloroformate (5.9 ml) under nitrogen at -40° C. to -30° C. The reaction mixture was stirred below -20° C. for 45 minutes. Then, triethylamine hydrochloride was filtered off and washed with cold tetrahydrofuran, and the filtrate was added as quickly as possible to a suspension of sodium borohydride (4.35 g) in tetrahydrofuran-water (8:1, 80 ml) at 0° C. with vigorous stirring. The stirring was continued at ambient temperature for 5 hours, followed by acidification of the solution to pH 5. The tetrahydrofuran was removed under reduced pressure, and the product was extracted with ethyl acetate. The ethyl acetate extracts were washed with water and brine, dried over magnesium sulfate and evaporated under reduced pressure. The residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1). The eluted fractions containing the desired product were collected and evaporated in vacuo to give methyl 3-hydroxymethyl-5-(pyrrol-1-yl)benzoate (7.33 g).

Workup

  1. filtrationThen, triethylamine hydrochloride was filtered off
  2. washwashed with cold tetrahydrofuran
  3. additionthe filtrate was added as quickly as
  4. additionpossible to a suspension of sodium borohydride (4.35 g) in tetrahydrofuran-water (8:1, 80 ml) at 0° C. with vigorous stirring
  5. waitThe stirring was continued at ambient temperature for 5 hours
  6. customThe tetrahydrofuran was removed under reduced pressure
  7. extractionthe product was extracted with ethyl acetate
  8. washThe ethyl acetate extracts were washed with water and brine
  9. dry with materialdried over magnesium sulfate
  10. customevaporated under reduced pressure
  11. customThe residue was purified by column chromatography on silica gel eluting with a mixture of chloroform and methanol (30:1)
  12. additionThe eluted fractions containing the desired product
  13. customwere collected
  14. customevaporated in vacuo

Sources & evidence

ORD record
ord-3ba40cd335054fbc85c100d737d445ae
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

Loading…