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

HRID 473352노트

반응식

HRID 473352 반응식
[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]

참가 물질

10

반응물 4

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

생성물 1

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

시약·촉매·용매 5

HCID 241Benzene용매HCID 887Methanol용매2회HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
40 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-eb84180e3bfe45c0bacc1f37a160b4b3
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08633315B2

반응 노트

불러오는 중…