Methyl iodide → HCID 22761120, compound

HRID 1704125Notes

Reaction equation

HRID 1704125 reaction equation
[CH:1](NC(C)C)(C)C.C([Li])CCC.[CH3:13][O:14][C:15](=[O:46])[CH:16]([O:35][C:36]1[CH:41]=[CH:40][C:39]([C:42]([CH3:45])([CH3:44])[CH3:43])=[CH:38][CH:37]=1)[C:17]1[CH:22]=[CH:21][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]2[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=2)=[CH:19][CH:18]=1.CI>O1CCCC1.CCCCCC.O>[C:42]([C:39]1[CH:38]=[CH:37][C:36]([O:35][C:16]([C:17]2[CH:18]=[CH:19][C:20]([O:23][CH2:24][CH2:25][CH2:26][O:27][C:28]3[CH:33]=[CH:32][C:31]([Cl:34])=[CH:30][CH:29]=3)=[CH:21][CH:22]=2)([CH3:1])[C:15]([O:14][CH3:13])=[O:46])=[CH:41][CH:40]=1)([CH3:43])([CH3:45])[CH3:44]

Participants

8

Reactant 4

HCID 6328Methyl iodideHCID 7912DiisopropylamineHCID 131711331HCID 131711331, compoundHCID 178418339Butyllithium

Product 1

HCID 22761120HCID 22761120, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
0 °C

Procedure

A solution of 2.7 ml of N,N-diisopropylamine in 15 ml of tetrahydrofuran under argon is stirred and cooled to 0° C. To the solution is added dropwise 8.5 ml of 2M n-butyllithium in hexane. The solution is cooled to -70° C. and a solution of 7.24 g of methyl(p-tert.-butylphenoxy){p-[3-(p-chlorophenoxy)propoxy]phenyl}acetate in 15 ml of tetrahydrofuran is added dropwise. After stirring at -70° C. for 30 minutes, 1.87 ml of methyl iodide is added and the mixture is stirred while slowly allowing to warm to room temperature. The mixture is poured into 100 ml of water and is extracted with ether. The ether extract is washed with 10% HCl, water, saturated NaCl and dried (MgSO4). The solvent is removed under reduced pressure to give 7.5 g of a clear gum. Chromatography over silica gel with dichloromethane-hexane as eluent gives 5.6 g of colorless gum.

Workup

  1. temperatureThe solution is cooled to -70° C.
  2. stirringthe mixture is stirred
  3. temperatureto warm to room temperature
  4. extractionis extracted with ether
  5. extractionThe ether extract
  6. washis washed with 10% HCl, water, saturated NaCl
  7. dry with materialdried (MgSO4)
  8. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-52355429870e4d07919a06df7a07dc4e
Source dataset
uspto-grants-1978_11
Patent number
US04125732

Reaction notes

Loading…