Allyl Alcohol → HCID 86701439, compound

HRID 2173905Notes

Reaction equation

HRID 2173905 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([OH:11])[CH:5]=[C:6]2[C:10]=1[NH:9][CH:8]=[CH:7]2.[CH2:12](O)[CH:13]=[CH2:14].C(C=P(CCCC)(CCCC)CCCC)#N>C1(C)C=CC=CC=1>[CH2:14]([O:11][C:4]1[CH:5]=[C:6]2[C:10](=[C:2]([CH3:1])[CH:3]=1)[NH:9][CH:8]=[CH:7]2)[CH:13]=[CH2:12]

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 4622928CyanomethylenetributylphosphoraneHCID 189327347-methyl-1H-indol-5-ol

Product 1

HCID 86701439HCID 86701439, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

7-Methyl-1H-indol-5-ol (5.2 g, 35.3 mmol) was dissolved in toluene (221 mL) and prop-2-en-1-ol (2.42 mL, 35.3 mmol) was added followed by cyanomethylenetributylphosphorane (21.32 g, 88 mmol). The reaction was heated at 100° C. After 1 hour the reaction was cooled to room temperature, concentrated and purified by silica gel flash chromatography (0:100 EtOAc:heptanes) to provide the title compound. MS (ESI+) m/z 188.15 (M+H).

Workup

  1. temperatureAfter 1 hour the reaction was cooled to room temperature
  2. concentrationconcentrated
  3. custompurified by silica gel flash chromatography (0:100 EtOAc:heptanes)

Sources & evidence

ORD record
ord-9fd0019ac0294890beed0c845195c9d4
Source dataset
uspto-grants-2015_06
Patent number
US09056874B2

Reaction notes

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