Methanol → HCID 86701479, compound

HRID 2173928Notes

Reaction equation

HRID 2173928 reaction equation
[CH2:1]([C:4]1[C:12]([OH:13])=[CH:11][C:10]([CH3:14])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH:2]=[CH2:3].CO.[C:17](C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH2:1]([C:4]1[C:12]([O:13][CH3:17])=[CH:11][C:10]([CH3:14])=[C:9]2[C:5]=1[CH:6]=[CH:7][NH:8]2)[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 887MethanolHCID 4622928CyanomethylenetributylphosphoraneHCID 86701441HCID 86701441, compound

Product 1

HCID 86701479HCID 86701479, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

4-Allyl-7-methyl-1H-indol-5-ol (Example 1-C) (2.77 g, 14.79 mmol) was dissolved in toluene (74.0 mL) and methanol (0.599 mL, 14.79 mmol) was added followed by cyanomethylenetributylphosphorane (8.93 g, 37.0 mmol). The reaction was heated at 110° C. for 1 hour. The reaction was cooled to room temperature and then concentrated. The residue was then absorbed onto silica and purified by silica gel flash chromatography (0-50% ethyl acetate/heptanes) to provide the title compound. MS (ESI+) m/z 202.17 (M+H).

Workup

  1. temperatureThe reaction was cooled to room temperature
  2. concentrationconcentrated
  3. customThe residue was then absorbed onto silica
  4. custompurified by silica gel flash chromatography (0-50% ethyl acetate/heptanes)

Sources & evidence

ORD record
ord-bc77a7fa17034b2eb8795bf6cb9cb811
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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