Hydrochloric Acid → Methyl 3-(4-((2-(2-(tosyloxy)ethyl)phenyl)ethynyl)phenyl)propanoate

HRID 2043026노트

반응식

HRID 2043026 반응식
[OH:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][C:12]1[CH:17]=[CH:16][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:14][CH:13]=1.[C:24]1([CH3:34])[CH:29]=[CH:28][C:27]([S:30](Cl)(=[O:32])=[O:31])=[CH:26][CH:25]=1.CCN(CC)CC.Cl>C(Cl)Cl.CCOC(C)=O.O>[S:30]([O:1][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]#[C:11][C:12]1[CH:13]=[CH:14][C:15]([CH2:18][CH2:19][C:20]([O:22][CH3:23])=[O:21])=[CH:16][CH:17]=1)([C:27]1[CH:28]=[CH:29][C:24]([CH3:34])=[CH:25][CH:26]=1)(=[O:32])=[O:31]

참가 물질

8

반응물 4

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 58319091Methyl 3-(4-((2-(2-hydroxyethyl)phenyl)ethynyl)phenyl)propanoate

생성물 1

HCID 58319136Methyl 3-(4-((2-(2-(tosyloxy)ethyl)phenyl)ethynyl)phenyl)propanoate

시약·촉매·용매 3

HCID 962Water용매HCID 6344Dichloromethane용매2회HCID 8857Ethyl Acetate용매

반응 조건

온도
10 °C

실험 절차

Methyl 3-(4-((2-(2-hydroxyethyl)phenyl)ethynyl)phenyl)propanoate (200 mg, 0.65 mmol) in CH2Cl2 (5 ml) was added para-toluenesulfonyl chloride (136 mg, 0.71 mmol). The mixture was cooled to 10° C. and NEt3 (72 mg, 0.71 mmol) in CH2Cl2 (1 ml) was added dropwise. The reaction was allowed to reach room temperature and reacted overnight. The reaction was added 1 M HCl (0.5 ml), water (10 ml) and extracted with CH2Cl2. The organic phases were combined, washed with aq. NaHCO3, dried over MgSO4, concentrated and purified by flash chromatography (SiO2, EtOAc:PE, 1:3) to give 153 mg (51%): Rf=0.20 (EtOAc:PE, 1:3); 1HNMR (CDCl3): δ 7.66 (d, J=6.3 Hz, 2H), 7.44-7.42 (m, 1H), 7.39 (d, J=6.3 Hz, 2H), 7.26-7.23 (m, 1H), 7.22-7.19 (m, 6H), 4.32 (t, J=5.1 Hz, 2H), 3.68 (s, 3H), 3.21 (t, J=5.7 Hz, 2H), 2.98 (t, J=6.0 Hz, 2H), 2.65 (t, J=5.4 Hz, 2H), 2.38 (s, 3H); 13CNMR (CDCl3): δ 173.1, 144.5, 141.2, 137.8, 133.0, 132.3, 131.7, 129.9, 129.7, 128.5, 128.5, 127.8, 127.0, 123.1, 120.9, 93.6, 86.8, 51.7, 35.4, 34.4, 30.9, 21.6.

후처리

  1. customto reach room temperature
  2. customreacted overnight
  3. extractionextracted with CH2Cl2
  4. washwashed with aq. NaHCO3
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated
  7. custompurified by flash chromatography (SiO2, EtOAc:PE, 1:3)
  8. customto give 153 mg (51%)

출처 및 근거

ORD 기록
ord-20b66f12a3684f889b2cd435fb8b3736
출처 데이터셋
uspto-grants-2013_11
특허 번호
US08586607B2

반응 노트

불러오는 중…