Diethyl Ether → HCID 20441012, compound

HRID 1633398Notes

Reaction equation

HRID 1633398 reaction equation
C[Mg]I.[Mg].[CH3:5]I.[CH2:7]([C:10]1(C(OC)=O)[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:19])[CH:16]=2)[CH2:11]1)[CH:8]=[CH2:9].[Cl-].[NH4+].CC[O:28][CH2:29][CH3:30]>>[CH2:7]([C:10]1([C:29]([OH:28])([CH3:30])[CH3:5])[CH2:18][C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Cl:19])[CH:16]=2)[CH2:11]1)[CH:8]=[CH2:9]

Participants

7

Reactant 6

HCID 3283Diethyl Ether2×HCID 6328Methyl iodideHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 20441020HCID 20441020, compoundHCID 178418373HCID 178418373, compound

Product 1

HCID 20441012HCID 20441012, compound

Procedure

To 150 ml of an anhydrous ether solution of methyl magnesium iodide prepared from 3.23 g of magnesium metal and 19.0 g of methyl iodide, with ice-cooling, was added dropwise a solution of 8.32 g of methyl 2-allyl-5-chloroindane-2-carboxylate in 10 ml of anhydrous ether. The mixture was stirred for 24 hours at room temperature to complete the reaction. The reaction mixture was poured into a mixture of saturated aqueous ammonium chloride solution and ice. After the ether layer was separated, the aqueous layer was extracted twice with ether. The ether layers were combined, washed with saturated sodium chloride solution, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain 7.56 g of the intended product.

Workup

  1. temperaturecooling
  2. customthe reaction
  3. customAfter the ether layer was separated
  4. extractionthe aqueous layer was extracted twice with ether
  5. washwashed with saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a786f52cd8c443a78c4b19af5634be70
Source dataset
uspto-grants-1984_10
Patent number
US04480118

Reaction notes

Loading…