Hydrochloric Acid → Methyl 4-[5-(2-methoxyvinyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 2248774Notes

Reaction equation

HRID 2248774 reaction equation
[CH3:1][C:2](C)([O-:4])C.[K+].[Cl-].[CH3:8]OC[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C([C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH2:41][CH2:42][CH3:43])[CH:36]=[C:35]2[CH2:44][C:45]1[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][C:46]=1[O:55][CH3:56])=O.Cl>O1CCCC1>[CH3:8][O:4][CH:2]=[CH:1][C:32]1[CH:33]=[C:34]2[C:38](=[CH:39][CH:40]=1)[N:37]([CH2:41][CH2:42][CH3:43])[CH:36]=[C:35]2[CH2:44][C:45]1[CH:54]=[CH:53][C:48]([C:49]([O:51][CH3:52])=[O:50])=[CH:47][C:46]=1[O:55][CH3:56]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 14882683Methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoateHCID 23665647Potassium tert-butoxide

Product 1

HCID 57325365Methyl 4-[5-(2-methoxyvinyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoateYield 56%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

A solution of potassium tert-butoxide (0.92 g) in dry tetrahydrofuran (10 ml) was added to a stirred suspension of (methoxymethyl)triphenylphosphonium chloride (2.8 g) in tetrahydrofuran (30 ml) under a nitrogen atmosphere, at ice-bath temperature. After 15 min, a solution of methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoate (2.0 g) in tetrahydrofuran (20 ml) was added dropwise. After 30 min, the mixture was poured onto water, and acidified with 1M hydrochloric acid. The mixture was extracted with ethyl acetate (twice), and the extract washed with water, and brine, then dried (MgSO4) and evaporated. The residue was dissolved in methylene chloride, ether was added to give a precipitate, and the isolated precipitate was purified by flash chromatography, eluting with 85:15 hexane:ethyl acetate, to give methyl 4-[5-(2-methoxyvinyl)-1-propylindol-3-ylmethyl]-3-methoxybenzoate (1.2 g, 56%) as an oil; partial NMR (300 MHz, DMSO-d6): 0.80(t, 3H, CH3), 1.70(m, 2H, CH2), 3.60 and 3.70(2xs, 3H, OCH3, E and Z isomers), 3.83(s, 3H, OCH3), 3.90(s, 3H, OCH3), 4.03(m, 4H, NCH2, ArCH2Ar').

Workup

  1. waitAfter 30 min
  2. additionthe mixture was poured onto water
  3. extractionThe mixture was extracted with ethyl acetate (twice), and the extract
  4. washwashed with water, and brine
  5. dry with materialdried (MgSO4)
  6. customevaporated
  7. dissolutionThe residue was dissolved in methylene chloride
  8. additionether was added
  9. customto give a precipitate
  10. customthe isolated precipitate was purified by flash chromatography
  11. washeluting with 85:15 hexane

Sources & evidence

ORD record
ord-7de8aa645b11488694a6f03b914a5d3a
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

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