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

HRID 2043026Notes

Reaction equation

HRID 2043026 reaction equation
[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]

Participants

8

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
10 °C

Procedure

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.

Workup

  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%)

Sources & evidence

ORD record
ord-20b66f12a3684f889b2cd435fb8b3736
Source dataset
uspto-grants-2013_11
Patent number
US08586607B2

Reaction notes

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