Indole-5-carbonitrile → Ethyl alpha-methylindol-5-acrylate

HRID 330166Notes

Reaction equation

HRID 330166 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)=O.C(C1C=C2C(=CC=1)NC=C2)#N.[C:23]([CH2:28][CH:29]=P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)([O:25][CH2:26][CH3:27])=[O:24]>>[CH3:29][C:28](=[CH:1][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[CH:6]2)[C:23]([O:25][CH2:26][CH3:27])=[O:24]

Participants

4

Reactant 3

HCID 27513Indole-5-carbonitrileHCID 589040Indole-5-carboxaldehydeHCID 12607919Ethyl 3-(triphenyl-lambda~5~-phosphanylidene)propanoate

Product 1

HCID 53676795Ethyl alpha-methylindol-5-acrylate

Procedure

Using a similar procedure to that described in Example 12, part c, except starting from 5-formylindole (prepared as described in the literature from 5-cyanoindole: F. Troxler, Helv. Chim. Acta., 51, 1616, (1968)), and using carbethoxyethylidene triphenylphosphorane, ethyl α-methylindol-5-acrylate was obtained (79%) as a low-melting white solid (mp about 50°); partial NMR(250 MHz, DMSO-d6): 1.28(t, 3H, CH2CH3), 2.13(d, J=1.0 Hz, 3H, CCH3), 4.19(q, 2H, CH2CH3), 6.49(m, 1H, H3 -indole), 11.28(br s, 1H, H1 -indole).

Workup

  1. customprepared

Sources & evidence

ORD record
ord-9a434223dc6f45f39e1285fc5fddf24f
Source dataset
uspto-grants-1990_01
Patent number
US04894386

Reaction notes

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