3-Fluorophenol → HCID 58213813, compound

HRID 1400678Notes

Reaction equation

HRID 1400678 reaction equation
[OH:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[CH:6]=[CH:5]1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[F:36][C:37]1[CH:38]=[C:39](O)[CH:40]=[CH:41][CH:42]=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[F:36][C:37]1[CH:42]=[C:41]([CH:40]=[CH:39][CH:38]=1)[O:1][CH2:2][CH2:3][N:4]1[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([C:13]([O:15][CH3:16])=[O:14])[CH:11]=2)[CH:6]=[CH:5]1

Participants

6

Reactant 4

HCID 97433-FluorophenolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 58213855HCID 58213855, compound

Product 1

HCID 58213813HCID 58213813, compoundYield 109.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 1-(2-hydroxyethyl)-1H-indole-6-carboxylate (0.14 g, 0.64 mmol) and Ph3P (0.25 mL, 0.96 mmol) and 3-fluorophenol (0.11 g, 0.96 mmol) in THF (10 mL) was added DIAD (0.19 mL, 0.96 mmol). The solution was stirred 1 hr at room temperature, then concentrated and subjected to flash chromatography (25% ethyl acetate/hexane) to provide 0.22 g (˜100%) of methyl 1-(2-(3-fluorophenoxy)ethyl)-1H-indole-6-carboxylate as a colorless oil.

Workup

  1. concentrationconcentrated

Sources & evidence

ORD record
ord-6468f96c5c454d5d8a59bb80951ecd0e
Source dataset
uspto-grants-2014_12
Patent number
US08906954B2

Reaction notes

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