Allyl Alcohol → HCID 15598953, compound

HRID 986808Notes

Reaction equation

HRID 986808 reaction equation
[H-].[Na+].[CH2:3](O)[CH:4]=C.[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2/[CH:24]=[CH:25]/[C:26]([O:28][CH3:29])=[O:27])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C1(C)C=CC=CC=1>[CH2:7]([O:14][C:15]1[CH:16]=[C:17]2[C:21](=[CH:22][CH:23]=1)[NH:20][CH:19]=[C:18]2/[CH:24]=[CH:25]/[C:26]([O:28][CH2:29][CH:3]=[CH2:4])=[O:27])[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1

Participants

5

Reactant 3

HCID 7858Allyl AlcoholHCID 24758Sodium hydrideHCID 86741953HCID 86741953, compound

Product 1

HCID 15598953HCID 15598953, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

17.45 g of a 55% w/w suspension of sodium hydride in mineral oil were suspended in 400 ml of toluene; to the resulting suspension were added 400 ml of allyl alcohol, whilst ice-cooling and under a nitrogen atmosphere. 122.93 g of methyl (E)-3-(5-benzyloxy-1H-indol-3-yl)acrylate were added thereto, and the mixture was heated under reflux for 10 minutes. The reaction mixture was then washed, in turn, with a saturated aqueous solution of citric acid, with a saturated aqueous solution of sodium hydrogen carbonate, with water and with a saturated aqueous solution of sodium chloride, and then dried over anhydrous magnesium sulfate. It was then condensed by evaporation under reduced pressure. The residue was purified by silica gel column chromatography using 20% v/v ethyl acetate in hexane as eluent, to give 100.12 g of the title compound as crystals melting at 73°-77° C.

Workup

  1. temperaturewhilst ice-cooling and under a nitrogen atmosphere
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 10 minutes
  4. washThe reaction mixture was then washed, in turn, with a saturated aqueous solution of citric acid, with a saturated aqueous solution of sodium hydrogen carbonate, with water and with a saturated aqueous solution of sodium chloride
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customcondensed
  7. customby evaporation under reduced pressure
  8. customThe residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-584fbf62197e448f87a8000531f2f25e
Source dataset
uspto-grants-1987_12
Patent number
US04716162

Reaction notes

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