Iodoethane → Methyl 2-(5-indanyloxy)-2-[p-(p-chlorophenoxy)phenyl]butyrate

HRID 1704082Notes

Reaction equation

HRID 1704082 reaction equation
Cl[C:2]1C=CC(OC(C2C=CC(OC3C=CC(Cl)=CC=3)=CC=2)(C)C(OC)=O)=C[CH:3]=1.[CH2:29]1[C:37]2[C:32](=[CH:33][C:34]([O:38][CH:39]([C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]4[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=4)=[CH:46][CH:45]=3)[C:40]([O:42][CH3:43])=[O:41])=[CH:35][CH:36]=2)[CH2:31][CH2:30]1.CN(C)P(N(C)C)(N(C)C)=O.C(I)C>O1CCCC1.O>[CH2:29]1[C:37]2[C:32](=[CH:33][C:34]([O:38][C:39]([C:44]3[CH:49]=[CH:48][C:47]([O:50][C:51]4[CH:56]=[CH:55][C:54]([Cl:57])=[CH:53][CH:52]=4)=[CH:46][CH:45]=3)([CH2:2][CH3:3])[C:40]([O:42][CH3:43])=[O:41])=[CH:35][CH:36]=2)[CH2:31][CH2:30]1

Participants

7

Reactant 4

HCID 6340IodoethaneHCID 12679HexamethylphosphoramideHCID 12531866Methyl (5-indanyloxy)[p-(p-chlorophenoxy)phenyl]acetateHCID 12531902Methyl 2-(p-chlorophenoxy)-2-[p-(p-chlorophenoxy)phenyl]propionate

Product 1

HCID 20392567Methyl 2-(5-indanyloxy)-2-[p-(p-chlorophenoxy)phenyl]butyrate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.015mole of lithium N,N-diisopropylamide (prepared as in example 55) in tetrahydrofuran is chilled to -65° C to -75° C. To the solution is added methyl (5-indanyloxy)[p-(p-chlorophenoxy)phenyl]acetate in tetrahydrofuran. To the mixture is added 4 ml of hexamethylphosphoramide and while chilling to -65° C to -75° C, 4.68 g of ethyl iodide is added. After 2 hr., the mixture is allowed to warm to room temperature and stir overnight. The mixture is poured into water and extracted with ether. The ether extracts are washed with 10% hydrochloric acid, water, saturated NaHCo3, saturated NaCl solution and dried (MgSO4). Evaporation of the solvent gives the product as an oil.

Workup

  1. temperaturewhile chilling to -65° C to -75° C
  2. extractionextracted with ether
  3. washThe ether extracts are washed with 10% hydrochloric acid, water, saturated NaHCo3, saturated NaCl solution
  4. dry with materialdried (MgSO4)
  5. customEvaporation of the solvent

Sources & evidence

ORD record
ord-883569cf83ec46b9a63bbfed15d02100
Source dataset
uspto-grants-1978_11
Patent number
US04125729

Reaction notes

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