Methyl iodide → HCID 19697527, compound

HRID 863225Notes

Reaction equation

HRID 863225 reaction equation
[CH3:1]I.[Mg].[CH2:4]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH:21]=[O:22])[CH2:12]1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>C(OCC)C>[CH2:4]([N:11]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH2:14][CH:13]([CH:21]([OH:22])[CH3:1])[CH2:12]1)[C:5]1[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5462224MagnesiumHCID 19697611HCID 19697611, compound

Product 1

HCID 19697527HCID 19697527, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

1.12 ml of methyliodide are added dropwise to 0.435 g of magnesium powder, suspended in 50 ml of diethyl ether, in the course of 10 min. After the mixture has been subsequently stirred for 0.5 h, 1.5 g of 1-benzyl-3(R,S)-formyl-1,2,3,4-tetrahydroquinoline, dissolved in 10 ml of diethyl ether, are added dropwise. The mixture is subsequently stirred for 0.5 h and then poured onto ice-water. The crude product extracted with methylene chloride is purified by means of FC over 150 g of silica gel (mobile phase B): Rf (B)=0.31; Rf (D)=0.15.

Workup

  1. additionare added dropwise
  2. stirringThe mixture is subsequently stirred for 0.5 h
  3. additionpoured onto ice-water
  4. extractionThe crude product extracted with methylene chloride
  5. customis purified by means of FC over 150 g of silica gel (mobile phase B)

Sources & evidence

ORD record
ord-e4498f56792440ab8a40f0b89ce9451c
Source dataset
uspto-grants-1998_02
Patent number
US05719141

Reaction notes

Loading…