3-Methylbenzyl alcohol → Ethyl 5-trimethylsilyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxylate

HRID 1804750Notes

Reaction equation

HRID 1804750 reaction equation
[CH3:1][Si:2]([CH3:18])([CH3:17])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2.[CH3:19][C:20]1[CH:21]=[C:22]([CH2:26]O)[CH:23]=[CH:24][CH:25]=1.C(C=P(CCCC)(CCCC)CCCC)#N>>[CH3:1][Si:2]([CH3:17])([CH3:18])[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([CH3:26])[CH:21]=1)[C:7]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:6]2

Participants

4

Reactant 3

HCID 114763-Methylbenzyl alcoholHCID 4622928CyanomethylenetributylphosphoraneHCID 66845842ethyl 5-trimethylsilyl-1H-indole-2-carboxylate

Product 1

HCID 58100930Ethyl 5-trimethylsilyl-1-[(3-methylphenyl)methyl]-1H-indole-2-carboxylate

Procedure

This compound was prepared according to a process similar to that described in step 5.1 by reacting ethyl 5-trimethylsilyl-1H-indole-2-carboxylate prepared according to the process described in step 10.4 with (3-methylphenyl)methanol in the presence of (cyanomethylene)tributylphosphorane (CMBP). The crude reaction product is then purified by flash chromatography on a column of silica gel to give the expected product.

Workup

  1. customThis compound was prepared
  2. customprepared
  3. customThe crude reaction product
  4. customis then purified by flash chromatography on a column of silica gel

Sources & evidence

ORD record
ord-f769644f47f24c3ab4a7668c4aa32e5c
Source dataset
uspto-grants-2013_01
Patent number
US08354425B2

Reaction notes

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