Dimethyl Sulfoxide → 2-(3-Chloropyridin-2-yl)propanal

HRID 2197603노트

반응식

HRID 2197603 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[Cl:11][C:12]1[C:13]([CH:18]([CH3:21])[CH2:19][OH:20])=[N:14][CH:15]=[CH:16][CH:17]=1>C(Cl)Cl>[Cl:11][C:12]1[C:13]([CH:18]([CH3:21])[CH:19]=[O:20])=[N:14][CH:15]=[CH:16][CH:17]=1

참가 물질

5

반응물 3

HCID 679Dimethyl SulfoxideHCID 65578Oxalyl chlorideHCID 674994232-(3-Chloropyridin-2-yl)propan-1-ol

생성물 1

HCID 866302832-(3-Chloropyridin-2-yl)propanal수율 97.1%

시약·촉매·용매 1

HCID 6344Dichloromethane용매3회

실험 절차

To a −78° C. solution of dimethylsulfoxide (4.04 g, 3.67 mL, 51.7 mmol) in methylene chloride (25 mL) was added a solution of oxalyl chloride (3.28 g, 2.26 mL, 25.9 mmol) in methylene chloride (5 mL) over two minutes. The reaction mixture was stirred for 15 minutes, and then a solution of the product of Example 38C (0.74 g, 4.31 mmol) in methylene chloride (25 mL) was added over 8 minutes. The reaction was allowed to warm to ambient temperature and quenched with water. The quenched reaction mixture was extracted with methylene chloride, and the organic layer washed with brine and concentrated. The residue was chromatographed on silica gel eluting with 25% ethyl acetate-hexane to give the title compound (0.71 g, 97%). 1H NMR (300 MHz, DMSO-d6) δ ppm 9.73 (s, 1H), 8.53 (dd, J=1.5, 4.7, 1H), 8.00 (dd, J=1.4, 8.1, 1H), 7.40 (dd, J=4.7, 8.1, 1H), 4.28 (q, J=7.0, 1H), 1.34 (d, J=7.0, 3H). MS (DCI) m/z 170 (M+H)+.

후처리

  1. customquenched with water
  2. customThe quenched reaction mixture
  3. extractionwas extracted with methylene chloride
  4. washthe organic layer washed with brine
  5. concentrationconcentrated
  6. customThe residue was chromatographed on silica gel eluting with 25% ethyl acetate-hexane

출처 및 근거

ORD 기록
ord-6bab20d7e07748a29a96d217f15aa6f6
출처 데이터셋
uspto-grants-2012_12
특허 번호
US08338603B2

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