p-Toluenesulfonic acid → HCID 58625013, 화합물

HRID 271632

반응식

HRID 271632 반응식
[O:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[Br:18][C:19]1[CH:20]=[C:21]([CH2:25][OH:26])[S:22][C:23]=1[CH3:24]>CO>[Br:18][C:19]1[CH:20]=[C:21]([CH2:25][O:26][CH:6]2[CH2:5][CH2:4][CH2:3][CH2:2][O:1]2)[S:22][C:23]=1[CH3:24]

참가 물질

5

반응물 3

HCID 6101p-Toluenesulfonic acidHCID 186148PyranHCID 59835954HCID 59835954, 화합물

생성물 1

HCID 58625013HCID 58625013, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

2.6 ml of 1,2-dihydropyrane and 0.2 g of p-toluene sulfonic acid were added to 5.4 g of 4-bromo-2 hydroxymethyl-5-methylthiophene 9 in 40 ml of methanol. The reaction mixture was stirred at room temperature for 24 hours. Methanol was distilled under vacuum and the remainder was distilled by an oil pump. The yield was 6.82 g of the product 10 (90%), Tmelt=125-130° C. (5 mm Hg), nd165=1.5610. Mass-spectrum, m/z: 291, [M]+. 1H NMR spectrum (CDCl3, δ, ppm, J/Hz): 1.45-1.95 (m, 6H, 3×CH2), 2.37 (s, 3H, CH3), 3.50-3.65 (m, 1H, CH), 3.80-4.0 (m, 1 H), 4.55-4.85 (m, 3H), 6.82 (s, 1 H, CH). The results found (%): C, 45.43; H, 5.20; S, 10.92. C11H15BrO2S. The results calculated (%): C, 45.37; H, 5.19; S, 11.01.

후처리

  1. distillationMethanol was distilled under vacuum
  2. distillationthe remainder was distilled by an oil pump
  3. customThe yield was 6.82 g of the product 10 (90%), Tmelt=125-130° C. (5 mm Hg), nd165=1.5610

출처 및 근거

ORD 기록
ord-35dc3632fd944ae9bb8116fddf50d5a9
출처 데이터셋
uspto-grants-2008_11
특허 번호
US07452950B2

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