Methyl iodide → HCID 15078759, compound

HRID 359151Notes

Reaction equation

HRID 359151 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][S:8]/[C:9](/[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[CH:10]\[C:11]([OH:13])=[O:12])=[CH:5][CH:4]=1.[CH2:22]1CCN2C(=NCCC2)CC1.IC>C(#N)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:7][S:8]/[C:9](/[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)=[CH:10]\[C:11]([O:13][CH3:22])=[O:12])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 15078758HCID 15078758, compound

Product 1

HCID 15078759HCID 15078759, compoundYield 79.2%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Z-3-(4'-Methoxybenzylthio)-3-phenyl-2-propenoic acid (5.46 g, 18.2 mmol) was suspended in 22 mL of dry acetonitrile. Addition of DBU (3.30 mL, 22.1 mmol) gave a clear yellow solution. The mixture was stirred in an ice bath and iodomethane (1.32, 21.2 mmol) was then added over 5 minutes. After an additional 15 minutes, the ice bath was removed and the solution was stirred for 1.25 hours. The reaction was poured into 100 mL of ethyl acetate and washed with 75 mL of water, 2×25 mL of 2N aqueous hydrochloric acid, 2×25 mL of saturated aqueous sodium bicarbonate, and 25 mL of saturated aqueous sodium chloride. The ethyl acetate solution was dried over sodium sulfate, decanted, and evaporated to give 4.53 g of crude methyl Z-3 (4'-methoxybenzylthio)-3-phenyl-2-propenoate as pale yellow crystals.

Workup

  1. customgave a clear yellow solution
  2. customthe ice bath was removed
  3. stirringthe solution was stirred for 1.25 hours
  4. additionThe reaction was poured into 100 mL of ethyl acetate
  5. washwashed with 75 mL of water, 2×25 mL of 2N aqueous hydrochloric acid, 2×25 mL of saturated aqueous sodium bicarbonate, and 25 mL of saturated aqueous sodium chloride
  6. dry with materialThe ethyl acetate solution was dried over sodium sulfate
  7. customdecanted
  8. customevaporated

Sources & evidence

ORD record
ord-9976f856fba3405580c2a81565fadea7
Source dataset
uspto-grants-1991_03
Patent number
US04999436

Reaction notes

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