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Sodium hydride → Ethyl acetate hexane

HRID 3340
Notes
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Reaction equation

HRID 3340 reaction equation
[OH:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[H-].[Na+].Br[CH:22]([CH3:27])[C:23]([O:25][CH3:26])=[O:24]>CN(C=O)C>[CH3:26][O:25][C:23](=[O:24])[CH:22]([O:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[C:5]([CH3:18])[N:6]2[CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[CH3:27].[CH3:22][CH2:23][O:24][C:2]([CH3:10])=[O:1].[CH3:9][CH2:10][CH2:2][CH2:3][CH2:4][CH3:5]
ParticipantsProcedureSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 95576Methyl 2-bromopropionateHCID 107523601-Benzyl-2-methyl-1H-indol-4-ol

Product 2

HCID 106396522-[[2-methyl-1-(phenylmethyl)-1H-indol-4-yl]oxy]propanoic acid methyl esterHCID 21226206Ethyl acetate hexaneYield 74%

Reagents, catalysts & solvents 1

HCID 6228
Dimethylformamide
Solvent

Procedure

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.

Sources & evidence

ORD record
ord-1c51dd5042944cafbcc75002bd31f9d1
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05733923

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes