Ethyl Bromide → (Z)-2-(Ethoxymethylene)-4,4-dimethylpentanal

HRID 473352ノート

反応式

HRID 473352 の反応式
[CH3:1][C:2]([CH3:8])([CH3:7])[CH2:3][CH2:4][CH:5]=[O:6].C[O-].[Na+].C([O:14][CH3:15])=O.Br[CH2:17][CH3:18]>C1COCC1.C1C=CC=CC=1.CN(C=O)C.O.CO>[CH2:17]([O:6]/[CH:5]=[C:4](/[CH2:3][C:2]([CH3:8])([CH3:7])[CH3:1])\[CH:15]=[O:14])[CH3:18]

参加物

10

反応物 4

HCID 6332Ethyl BromideHCID 7865Methyl formateHCID 10942334Sodium MethoxideHCID 110623434,4-Dimethylpentanal

生成物 1

HCID 86627013(Z)-2-(Ethoxymethylene)-4,4-dimethylpentanal

試薬・触媒・溶媒 5

HCID 241Benzene溶媒HCID 887Methanol溶媒2 回HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
40 °C

実験手順

4,4-Dimethylpentanal (4.20 g, 36.8 mmol, Step 2) in 36 mL of THF was added over 4 hours by syringe pump to a solution of sodium methoxide, 25 wt. % in methanol (15.1 ml, 66.2 mmol), 15 mL of methanol, and methyl formate (166 ml, 2685 mmol). Following the addition, the reaction was diluted with benzene (50 mL) and DMF (40 mL). The solvents were distilled off at 90° C. leaving the DMF and residual benzene. Bromoethane (11.0 ml, 147 mmol) was added and the solution was heated at 40° C. for 48 hrs and then cooled. The solution was diluted with water, and the reaction was extracted with ether. The combined organic layers were washed with water, brine, and dried over magnesium sulfate, filtered and concentrated to afford the title compound.

後処理

  1. additionthe addition
  2. distillationThe solvents were distilled off at 90° C.
  3. customleaving the DMF and residual benzene
  4. temperaturecooled
  5. extractionthe reaction was extracted with ether
  6. washThe combined organic layers were washed with water, brine
  7. dry with materialdried over magnesium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-eb84180e3bfe45c0bacc1f37a160b4b3
出典データセット
uspto-grants-2014_01
特許番号
US08633315B2

反応ノート

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