Potassium Cyanide → (+/-)-cis-2,2-Dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

HRID 893487

反応式

HRID 893487 の反応式
[C-:1]#[N:2].[K+].[CH2:4]([C@@H:7]([OH:12])[CH2:8][C@@H:9]1[CH2:11][O:10]1)[CH:5]=[CH2:6].[CH:13](O)([CH3:15])[CH3:14].O>>[CH3:14][C:13]1([CH3:15])[O:10][C@@H:9]([CH2:11][C:1]#[N:2])[CH2:8][C@@H:7]([CH2:4][CH:5]=[CH2:6])[O:12]1

参加物

4

反応物 3

HCID 9032Potassium CyanideHCID 13895984(R*,R*)-alpha-2-propenyloxiraneethanolHCID 21889133Propan-2-ol--water (1/1)

生成物 1

HCID 15045109(+/-)-cis-2,2-Dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile

実験手順

Potassium cyanide, 1.3 g (20 mmol), is added to a room temperature solution of (R*,R*)-α-2-propenyloxiraneethanol, 2.56 g (20 mmol), in 25 mL of 4:1 isopropanol-water. The solution is stirred for 20 hours at ambient temperature, concentrated, and partitioned between ethyl acetate and brine. The aqueous layer is extracted 2x with ethyl acetate and the combined ethyl acetate extracts are washed with brine and dried (magnesium sulfate). The crude product is dissolved in 20 mL of 2,2-dimethoxypropane, camphorsulfonic acid is added and the solution stirred for 18 hours at room temperature. Concentration and flash chromatography provides 1.30 g of (±)-cis-2,2-dimethyl-6-(2-propenyl)-1,3-dioxane-4-acetonitrile.

後処理

  1. concentrationconcentrated
  2. custompartitioned between ethyl acetate and brine
  3. extractionThe aqueous layer is extracted 2x with ethyl acetate
  4. washthe combined ethyl acetate extracts are washed with brine
  5. dry with materialdried (magnesium sulfate)
  6. dissolutionThe crude product is dissolved in 20 mL of 2,2-dimethoxypropane
  7. additioncamphorsulfonic acid is added
  8. stirringthe solution stirred for 18 hours at room temperature
  9. concentrationConcentration and flash chromatography

出典と根拠

ORDレコード
ord-6d9cbb5d233a4a859f1d074b22fbfb4d
出典データセット
uspto-grants-1992_06
特許番号
US05124482

関連ノート

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