tert-Butyl (triphenylphosphoranylidene) acetate → methyl E-4-[5-[2-(t-butoxycarbonyl)vinyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate

HRID 2248779Notes

Reaction equation

HRID 2248779 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH3:14])[CH:7]=[C:6]2[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27])=O.C1(P(=[CH:47][C:48]([O:50][C:51]([CH3:54])([CH3:53])[CH3:52])=[O:49])(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>>[C:51]([O:50][C:48](/[CH:47]=[CH:1]/[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:12][CH2:13][CH3:14])[CH:7]=[C:6]2[CH2:15][C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][C:17]=1[O:26][CH3:27])=[O:49])([CH3:54])([CH3:53])[CH3:52]

Participants

3

Reactant 2

HCID 256127tert-Butyl (triphenylphosphoranylidene) acetateHCID 14882683Methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoate

Product 1

HCID 19994980methyl E-4-[5-[2-(t-butoxycarbonyl)vinyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate

Procedure

Using a similar procedure to that described in Example 8, part e, except starting from methyl 4-(5-formyl-1-propylindol-3-ylmethyl)-3-methoxybenzoate, and using tert-butyl (triphenylphosphoranylidene)acetate, methyl E-4-[5-[2-(t-butoxycarbonyl)vinyl]-1-propylindol-3-ylmethyl]-3-methoxybenzoate was obtained (98%) as a viscous oil; partial NMR (250 MHz, DMSO-d6): 0.81(t, 3H, CH2CH3), 1.48(s, 9H, C(CH3)3), 1.75(m, 2H, CH2CH3), 3.82(s, 3H, OCH3), 3.91(s, 3H, OCH3), 6.38(d, J=15.8 Hz, 1H, CH=CH), 7.6(d, J=15.8 Hz, 1H, CH=CH).

Sources & evidence

ORD record
ord-066baca738314b7e99c3d18c290fb0f9
Source dataset
uspto-grants-1991_08
Patent number
US05041460

Reaction notes

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