Methyl iodide → HCID 58031832, compound

HRID 535274Notes

Reaction equation

HRID 535274 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]([OH:22])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:11][CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.I[CH3:24]>C1(C)C=CC=CC=1.[Ag]=O>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH:15]([O:22][CH3:24])[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 6328Methyl iodide2×HCID 15890182ethyl 3-(4-(benzyloxy)phenyl)-3-hydroxypropanoate

Product 1

HCID 58031832HCID 58031832, compound

Reagents, catalysts & solvents 2

HCID 92152Silver(II) oxideCatalystHCID 1140TolueneSolvent

Conditions

Temperature
70 °C

Procedure

40 g of ethyl 3-(4-benzyloxyphenyl)-3-hydroxypropionate, 75 g of silver oxide and 83 ml of iodomethane were initially charged in 350 ml of toluene and stirred in a closed vessel at bath temperature 70° C. for 24 hours. Then a further 20 ml of iodomethane were added and the mixture was stirred at bath temperature 70° C. for a further 48 hours. The reaction mixture was filtered through a short silica gel layer and washed with toluene, and then the toluene was removed under reduced pressure. The residue was purified on silica gel with the eluent ethyl acetate:n-heptane=1:2. This gave 22.9 g of ethyl 3-(4-benzyloxyphenyl)-3-methoxypropionate.

Workup

  1. stirringthe mixture was stirred at bath temperature 70° C. for a further 48 hours
  2. filtrationThe reaction mixture was filtered through a short silica gel layer
  3. washwashed with toluene
  4. customthe toluene was removed under reduced pressure
  5. customThe residue was purified on silica gel with the eluent ethyl acetate

Sources & evidence

ORD record
ord-e14e4bf4678f4a8285dcab77f35b3af4
Source dataset
uspto-grants-2014_10
Patent number
US08859494B2

Reaction notes

Loading…