Reaktion #3436

ord-1c51dd5042944cafbcc75002bd31f9d1

Reaktionsgleichung

Cc1cc2c(O)cccc2n1Cc1ccccc1
4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole
[H-].[Na+]
NaH
COC(=O)C(C)Br
methyl 2-bromopropionate
COC(=O)C(C)Oc1cccc2c1cc(C)n2Cc1ccccc1
2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester
CCCCCC.CCOC(C)=O
EtOAc hexane
Ausbeute 74.0%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Vorschrift

4-Hydroxy-2-methyl-1-(phenylmethyl)-1H-indole (483 mg, 2.0 mmol) was reacted with 82 mg (2.0 mmol) of 60% NaH/mineral oil in 20 mL of DMF and then with 0.22 mL (2.0 mmol) of dl-methyl 2-bromopropionate as described in Example 1, Part E to give after chromatography on silica gel eluting with 20% EtOAc/hexane 480 mg (74% yield) of dl-2-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl ester.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US05733923uspto-grants-1998_03