Dichloromethane → Didodecyl 2-(thiophen-3-yl)malonate

HRID 335353노트

반응식

HRID 335353 반응식
[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:10]([OH:12])=[O:11])[C:7]([OH:9])=[O:8])=[CH:2]1.[CH2:13](O)[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24].CS(O)(=O)=O.C(Cl)Cl>C1COCC1>[S:1]1[CH:5]=[CH:4][C:3]([CH:6]([C:7]([O:9][CH2:24][CH2:23][CH2:22][CH2:21][CH2:20][CH2:19][CH2:18][CH2:17][CH2:16][CH2:15][CH2:14][CH3:13])=[O:8])[C:10]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH3:24])=[O:11])=[CH:2]1

참가 물질

6

반응물 4

HCID 6344DichloromethaneHCID 6395Methanesulfonic AcidHCID 81931-DodecanolHCID 887822-(Thiophen-3-yl)propanedioic acid

생성물 1

HCID 70983275Didodecyl 2-(thiophen-3-yl)malonate수율 69%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

In a one-necked flask, 3-thienylmalonic acid (10.0 g, 53.7 mmol) and 1-dodecanol (4 eq., 40.0 g, 215 mmol) were dissolved in THF (80 mL) at room temperature. To this solution was added methanesulphonic acid (1.99 g, 20.7 mmol). The reaction mixture was stirred at room temperature for 3 days. The solvent was then evaporated at 40° C. The residue was re-dissolved in CH2Cl2 to form a solution, which was loaded onto a column (eluent: CH2Cl2) to give didodecyl 2-(thiophen-3-yl)malonate (yield: 18.0 g, 69%). 1H NMR (CDCl3): 0.9 (6H, t), 1.3 (36H, m), 1.7 (4H, m), 4.2 (4H, t), 4.8 (1H, s), 7.2 (1H, d), 7.3 (1H, d), 7.4 (1H, s).

후처리

  1. customThe solvent was then evaporated at 40° C
  2. dissolutionThe residue was re-dissolved in CH2Cl2
  3. customto form a solution, which

출처 및 근거

ORD 기록
ord-c14abc847f884fe880e957398e1c90c8
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08883954B2

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