Triethylamine → Methanesulfonic acid 2-phenyl-allyl ester

HRID 77327

반응식

HRID 77327 반응식
[C:1]1([C:7](=[CH2:10])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(N(CC)CC)C.[CH3:18][S:19](Cl)(=[O:21])=[O:20]>ClCCl>[C:1]1([C:7](=[CH2:10])[CH2:8][O:9][S:19]([CH3:18])(=[O:21])=[O:20])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 80106beta-Methylenephenethyl alcohol

생성물 1

HCID 86653276Methanesulfonic acid 2-phenyl-allyl ester수율 94.8%

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

To a well stirred solution of 2-phenyl-prop-2-en-1-ol (700 mg, 5.22 mmol) in dichlorometane (10 mL) at 0° C. is added triethylamine (0.945 mL, 6.78 mmol) and methylsulfonyl chloride (0.424 mL, 5.48 mmol). The reaction is allowed to stir for 10 min, warmed to room temperature and is stirred for 30 min. The reaction is quenched by the addition of a saturated aqueous solution of ammonium chloride and extracted several times with ethyl acetate. The organic layers are combined, washed with 1 N hydrochloric acid, brine, dried over magnesium sulfate, filtered and concentrated in vacuo. The residue is purified via silica gel chromatography (10% ethyl acetate in hexanes) to yield the title compound (1.07 g, 4.95 mmol).

후처리

  1. stirringis stirred for 30 min
  2. customThe reaction is quenched by the addition of a saturated aqueous solution of ammonium chloride
  3. extractionextracted several times with ethyl acetate
  4. washwashed with 1 N hydrochloric acid, brine
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue is purified via silica gel chromatography (10% ethyl acetate in hexanes)

출처 및 근거

ORD 기록
ord-70d466be53c046c28b3842119842f724
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841291B2

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