Hydrochloric Acid → 4-Methyl-3-nitrobenzyl methanesulfonate

HRID 1071527

반응식

HRID 1071527 반응식
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][OH:9])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11].C(N(CC)CC)C.[CH3:20][S:21](Cl)(=[O:23])=[O:22].Cl>C(Cl)Cl.CCCCCC.C(OCC)(=O)C>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][O:9][S:21]([CH3:20])(=[O:23])=[O:22])=[CH:4][C:3]=1[N+:10]([O-:12])=[O:11]

참가 물질

7

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 1234974-Methyl-3-nitrobenzyl alcohol

생성물 1

HCID 208002884-Methyl-3-nitrobenzyl methanesulfonate

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 21226206Ethyl acetate hexane용매

반응 조건

온도
0 °C

실험 절차

(4-Methyl-3-nitro-phenyl)-methanol (3.00 g, 17.95 mmol) was taken up in anhydrous DCM, under argon, and triethyl amine (5.45 g, 53.85 mmol, 7.51 mL) was added. The solution was cooled to 0° C. and methanesulfonyl chloride (2.26 g, 19.74 mmol, 1.53 mL) was added slowly via syringe. The solution was allowed to warm to room temp and stir for 12 h. The reaction mixture poured into 1N HCl and the aqueous layer was extracted three times with ethyl acetate. The combined organic layers were washed with water, brine and dried over anhydrous magnesium sulfate. The solution was filtered and the solvent removed under reduced pressure. The product was isolated by flash chromatography. (5:1 hexane/ethyl acetate) Yield 2.00 g. 1H NMR (CDCl3, 300 MHz): δ 2.62 (s, 3H), 4.61 (s, 2H), 7.36 (d, J=8 Hz, 1H), 7.36 (d, J=8 Hz, 1H), 8.02 (s, 1H).

후처리

  1. temperatureto warm to room temp
  2. extractionthe aqueous layer was extracted three times with ethyl acetate
  3. washThe combined organic layers were washed with water, brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationThe solution was filtered
  6. customthe solvent removed under reduced pressure
  7. customThe product was isolated by flash chromatography

출처 및 근거

ORD 기록
ord-32bde081ba954d259527e036ca3c4b70
출처 데이터셋
uspto-grants-2005_06
특허 번호
US06906067B2

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