Ethyl Acetate → methyl E-4-[5-[2-(t-butoxycarbonyl)-1-propenyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate

HRID 330174Notes

Reaction equation

HRID 330174 reaction equation
C1(P(=[C:20]([CH3:28])[C:21]([O:23][C:24]([CH3:27])([CH3:26])[CH3:25])=[O:22])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH3:40])[CH:35]=[C:34]2[CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][C:43]=1[O:52][CH3:53])=O.[C:54](OCC)(=O)C>O1CCOCC1>[C:24]([O:23][C:21](/[C:20](/[CH3:28])=[CH:54]/[C:31]1[CH:32]=[C:33]2[C:37](=[CH:38][CH:39]=1)[N:36]([CH3:40])[CH:35]=[C:34]2[CH2:41][C:42]1[CH:51]=[CH:50][C:45]([C:46]([O:48][CH3:49])=[O:47])=[CH:44][C:43]=1[O:52][CH3:53])=[O:22])([CH3:25])([CH3:26])[CH3:27]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 10916149t-Butyl (triphenylphosphoranylidene)propionateHCID 14882555Methyl 4-(5-formyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 14882556methyl E-4-[5-[2-(t-butoxycarbonyl)-1-propenyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoateYield 90%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of t-butyl (triphenylphosphoranylidene)propionate (10.41 g) and methyl 4-(5-formyl-1-methylindol-3-ylmethyl)-3-methoxybenzoate (4.5 g) in dry dioxane (60 ml) was stirred and heated at 100° for 18 hr, under an atmosphere of nitrogen. After ethyl acetate (100 ml) was added to the cooled reaction solution, solids were removed by filtration and the filtrate evaporated. The residual dark oil was purified by flash chromatography, eluting with 45:50:5 hexane: methylene chloride:ethyl acetate, to give methyl E-4-[5-[2-(t-butoxycarbonyl)-1-propenyl]-1-methylindol-3-ylmethyl]-3-methoxybenzoate (5.4 g, 90%) as a white foam: partial NMR (250 MHz, DMSO-6): 1.49 (s, 9H, t-butyl), 2.01(d, J=1.0 Hz, 3H, CCH3), 3.74(s, 3H), 3.82(s, 3H), 3.90(s, 3H), 4.05(s, 2H, ArCH2Ar').

Workup

  1. temperatureheated at 100° for 18 hr, under an atmosphere of nitrogen
  2. customwere removed by filtration
  3. customthe filtrate evaporated
  4. customThe residual dark oil was purified by flash chromatography
  5. washeluting with 45:50:5 hexane

Sources & evidence

ORD record
ord-218a44009ddd495586e58c9bb38047b0
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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