Dimethyl Sulfoxide → 2-Heptyloxy-4-iodobenzaldehyde

HRID 1171432

반응식

HRID 1171432 반응식
CS(C)=O.C(Cl)(=O)C(Cl)=O.[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1[CH2:26][OH:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17].C(N(CC)CC)C>ClCCl.O>[CH2:11]([O:18][C:19]1[CH:24]=[C:23]([I:25])[CH:22]=[CH:21][C:20]=1[CH:26]=[O:27])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH3:17]

참가 물질

7

반응물 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 68768142(2-Heptyloxy-4-iodophenyl)methanol

생성물 1

HCID 860544942-Heptyloxy-4-iodobenzaldehyde

시약·촉매·용매 2

HCID 962Water용매HCID 6344Dichloromethane용매3회

실험 절차

A solution of dimethyl sulfoxide (DMSO) (41.4 mmol, 3 ml) in dichloromethane (10 ml) is added to a solution of 1.8 ml of oxalyl chloride (20.7 mmol) in 55 ml of dichloromethane, dropwise, at −78° C. After stirring for 15 minutes, a solution of (2-heptyloxy-4-iodophenyl)methanol obtained in Step b (6.55 g, 18.8 mmol) in 25 ml of dichloromethane is added dropwise. After stirring for 20 minutes, 14 ml of triethylamine are added. After stirring for 2 hours, the reaction medium is hydrolysed by addition of water. The desired product is extracted by addition of ethyl acetate. The organic phase is washed with water, dried with magnesium sulfate and concentrated using a rotary evaporator. After evaporation of the solvents, 6.49 g (100%) of the expected compound are recovered in the form of a yellow solid.

후처리

  1. customat −78° C
  2. stirringAfter stirring for 20 minutes
  3. stirringAfter stirring for 2 hours
  4. extractionThe desired product is extracted by addition of ethyl acetate
  5. washThe organic phase is washed with water
  6. dry with materialdried with magnesium sulfate
  7. concentrationconcentrated
  8. customa rotary evaporator
  9. customAfter evaporation of the solvents, 6.49 g (100%) of the expected compound
  10. customare recovered in the form of a yellow solid

출처 및 근거

ORD 기록
ord-98427741d4fd48dd8ff517848ac386b8
출처 데이터셋
uspto-grants-2010_11
특허 번호
US07829588B2

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