Tetrahydrofuran → HCID 19097333, compound

HRID 486064Notes

Reaction equation

HRID 486064 reaction equation
C(OC(C([C:8]1[NH:9][C:10]2[C:15]([CH:16]=1)=[CH:14][C:13]([O:17][CH2:18][C:19]1[CH:28]=[CH:27][C:26]3[C:21](=[CH:22][CH:23]=[CH:24][CH:25]=3)[N:20]=1)=[CH:12][CH:11]=2)C)=O)C.[OH2:29].[OH-].[Li+].[O:32]1[CH2:36][CH2:35][CH2:34]C1>>[N:20]1[C:21]2[C:26](=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:27]=[CH:28][C:19]=1[CH2:18][O:17][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]([CH2:34][CH2:35][C:36]([OH:32])=[O:29])[CH:8]=[CH:16]2

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 168937Lithium hydroxide, monohydrateHCID 67795053HCID 67795053, compound

Product 1

HCID 19097333HCID 19097333, compound

Procedure

A mixture of 1-ethoxycarbonylethyl-5-(2-quinolylmethoxy)indole (2.0 g) and lithium hydroxide monohydrate (0.9 g) in aqueous tetrahydrofuran was refluxed for 3 hours. The cooled mixture was extracted with ethyl acetate and the organic layer was washed with water, dried over magnesium sulfate, and concentrated in vacuo. The crude product was chromatographed on silica gel eluting with 50%-ethyl acetate in n-hexanes to yield the titled product, m.p. 157°-160° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. extractionThe cooled mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated in vacuo
  6. customThe crude product was chromatographed on silica gel eluting with 50%-ethyl acetate in n-hexanes

Sources & evidence

ORD record
ord-11b35ace9f9841f5964075823dd73bad
Source dataset
uspto-grants-1994_03
Patent number
US05290788

Reaction notes

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