Sodium Iodide → HCID 591785, compound

HRID 845490Notes

Reaction equation

HRID 845490 reaction equation
[C:1]([CH:6]1[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:13])([O:3][CH2:4][CH3:5])=[O:2].[I-].[Na+].[H-].[Na+].[H][H].Br[CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23]>C1(C)C=CC=CC=1.O>[C:1]([C:6]1([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][C:7]1=[O:13])([O:3][CH2:4][CH3:5])=[O:2]

Participants

8

Reactant 5

HCID 5238Sodium IodideHCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 279795ethyl 2-oxocycloheptanecarboxylateHCID 178418361HCID 178418361, compound

Product 1

HCID 591785HCID 591785, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
65 °C

Procedure

For example, a solution of 2-carboethoxy-cycloheptanone (I) (92.2 g, 0.5 mole) in toluene (1.6 l) is treated with sodium iodide (1 g) and 60% sodium hydride in mineral oil (23.3 g, 0.58 mole). The mixture is heated at 110° C. until hydrogen gas evolution drops off. Ethyl bromoacetate (98.0 g, 0.58 mole) is added dropwise and the mixture is warmed to 65° C. for 18 hours. The mixture is cooled and water (500 ml) is added. The layers are separated and the aqueous layer is extracted with toluene (2×1 l). The extracts are dried (MgSO4) and filtered. The filtrate is concentrated at reduced pressure and distilled to yield pure 2-carboethoxy-2-carboethoxymethylcycloheptanone (II) with a bp 182°-185° C. at 13 mm.

Workup

  1. temperatureThe mixture is cooled
  2. customThe layers are separated
  3. extractionthe aqueous layer is extracted with toluene (2×1 l)
  4. dry with materialThe extracts are dried (MgSO4)
  5. filtrationfiltered
  6. concentrationThe filtrate is concentrated at reduced pressure
  7. distillationdistilled

Sources & evidence

ORD record
ord-14716f713d934adf8825afd022f969f1
Source dataset
uspto-grants-1988_07
Patent number
US04758585

Reaction notes

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