2-((Tert-butyldimethylsilyl)oxy)acetaldehyde → (E)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-butenoic Acid Ethyl Ester

HRID 1092795노트

반응식

HRID 1092795 반응식
[Si:1]([O:8][CH2:9][CH:10]=O)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].[CH2:12]([O:14][C:15](=[O:36])[CH2:16]P(C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[CH3:13]>C1(C)C=CC=CC=1>[Si:1]([O:8][CH2:9]/[CH:10]=[CH:16]/[C:15]([O:14][CH2:12][CH3:13])=[O:36])([C:4]([CH3:5])([CH3:6])[CH3:7])([CH3:2])[CH3:3]

참가 물질

4

반응물 2

HCID 41877882-((Tert-butyldimethylsilyl)oxy)acetaldehydeHCID 178473137HCID 178473137, 화합물

생성물 1

HCID 10490523(E)-4-[[(1,1-Dimethylethyl)dimethylsilyl]oxy]-2-butenoic Acid Ethyl Ester수율 98%

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

2-(Tert-butyldimethylsilyloxy)acetaldehyde (10.0 g, 57.3 mmol) was added to a solution of (2-ethoxy-2-oxoethyl)triphenylphosphorane (20.0 g, 57.4 mmol) in 150 mL toluene, the mixture was stirred at RT overnight and then heated to 50° C. for 5 hrs. Solvents were removed and the residue was suspended in 400 mL of hexane. The solution was filtered, the filtrate was concentrated to give the product 3A as a colorless liquid 13.7 g (98%). 1H NMR (400 MHz, CDCl3) δ ppm 0.08 (s, 6H), 0.92 (s, 9H), 1.30 (t, 3H, 6 Hz), 4.21 (q, 2H, 6 Hz), 4.34 (dt, 2H), 6.09 (dt, 1H), 7.00 (dt, 1H); ESI-MS:m/z 245.3 (M+H)+, HPLC retention time: T=2.737 min (analytical-3).

후처리

  1. temperatureheated to 50° C. for 5 hrs
  2. customSolvents were removed
  3. filtrationThe solution was filtered
  4. concentrationthe filtrate was concentrated

출처 및 근거

ORD 기록
ord-94240a058e7942be8af1d7d36fd48d34
출처 데이터셋
uspto-grants-2012_03
특허 번호
US08129538B1

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