HCID 54251209, compound → HCID 53903795, compound

HRID 1704175Notes

Reaction equation

HRID 1704175 reaction equation
[CH2:1]1[O:9][C:8]2[CH:7]=[CH:6][C:5]([CH2:10][CH2:11][CH:12]=[CH:13][CH2:14][CH2:15]Br)=[CH:4][C:3]=2[O:2]1.[CH2:17]([O:19][C:20](=[O:25])[CH2:21][C:22]([CH3:24])=[O:23])[CH3:18].[Li]>CN(C)C=O>[C:22]([CH:21]([CH2:15][CH2:14][CH:13]=[CH:12][CH2:11][CH2:10][C:5]1[CH:6]=[CH:7][C:8]2[O:9][CH2:1][O:2][C:3]=2[CH:4]=1)[C:20]([O:19][CH2:17][CH3:18])=[O:25])(=[O:23])[CH3:24]

Participants

4

Reactant 2

HCID 54251209HCID 54251209, compoundHCID 87089452HCID 87089452, compound

Product 1

HCID 53903795HCID 53903795, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 28.3 g. (0.1 mole) of 6-(3,4-methylenedioxyphenyl)-3-hexenyl bromide and 21 g. (0.15 mole) of lithium ethylacetoacetate in 200 ml. of dimethylformamide was heated under nitrogen with stirring at 55°-60° C. for 2 days. The reaction mixture was concentrated in vacuo and the residue partitioned between water and methylene dichloride. The methylene dichloride layer was washed with 5% aqueous sulfuric acid, water, 5% aqueous sodium bicarbonate and water, and dried over anhydrous magnesium sulfate. The ether solution was concentrated to afford ethyl 2-acetyl-8-(3,4-methylenedioxyphenyl)-5-octenoate as a yellow oil, used directly in the following reaction.

Workup

  1. additionA mixture of 28.3 g
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue partitioned between water and methylene dichloride
  4. washThe methylene dichloride layer was washed with 5% aqueous sulfuric acid, water, 5% aqueous sodium bicarbonate and water
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationThe ether solution was concentrated

Sources & evidence

ORD record
ord-527b3ff55de64ecfb2f0526040837a93
Source dataset
uspto-grants-1978_11
Patent number
US04125714

Reaction notes

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