Tetramethylurea → 3,5-Heptanedione, 4-[6-(1,3-benzodioxol-5-yl)-3-ethyl-3-hexenyl]-

HRID 426876

反応式

HRID 426876 の反応式
[Li].[CH3:2][CH2:3][C:4](=[O:10])[CH2:5][C:6](=[O:9])[CH2:7][CH3:8].CN(C)C(=O)N(C)C.[CH2:19]([C:21](=[CH:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)[CH2:22][CH2:23]I)[CH3:20]>>[CH2:19]([C:21](=[CH:25][CH2:26][CH2:27][C:28]1[CH:33]=[CH:32][C:31]2[O:34][CH2:35][O:36][C:30]=2[CH:29]=1)[CH2:22][CH2:23][CH:5]([C:4](=[O:10])[CH2:3][CH3:2])[C:6](=[O:9])[CH2:7][CH3:8])[CH3:20]

参加物

5

反応物 4

HCID 12437TetramethylureaHCID 819233,5-HeptanedioneHCID 3028194LithiumHCID 543734513-Ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl iodide

生成物 1

HCID 5143023,5-Heptanedione, 4-[6-(1,3-benzodioxol-5-yl)-3-ethyl-3-hexenyl]-

実験手順

A solution of 15 g. of the lithium salt of 3,5-heptanedione (prepared as described in Example 8 below) in 100 ml. of tetramethylurea was stirred under nitrogen at room temperature, and 10 g. of 3-ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl iodide (Preparation D1) was added. The reaction mixture was stirred for forty-eight hours, then concentrated to remove the solvent, and the residue slurried in ether and treated with excess glacial acetic acid. Water was added, the ether layer separated, washed with water and concentrated. The residue was distilled in a molecular still to remove volatile material at 110° C. (0.001 mml.), and the non-volatile residue was chromatographed on 10 g. of activated magnesium silicate in benzene solution and eluted with ethyl acetate to give 4-[3-ethyl-6-(3,4-methylenedioxyphenyl)-3-hexenyl]-3,5-heptanedione as a yellow oil.

後処理

  1. concentrationconcentrated
  2. customto remove the solvent
  3. additionthe residue slurried in ether and treated with excess glacial acetic acid
  4. additionWater was added
  5. customthe ether layer separated
  6. washwashed with water
  7. concentrationconcentrated
  8. distillationThe residue was distilled in a molecular still
  9. customto remove volatile material at 110° C. (0.001 mml.)
  10. customthe non-volatile residue was chromatographed on 10 g
  11. washof activated magnesium silicate in benzene solution and eluted with ethyl acetate

出典と根拠

ORDレコード
ord-e01a204d32824ab3a4304798e5cd17ea
出典データセット
uspto-grants-1979_10
特許番号
US04171378

関連ノート

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