Triethylamine → HCID 86667300, compound

HRID 2406953Notes

Reaction equation

HRID 2406953 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[OH:6][CH:7]([C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C>ClCCl.C(OCC)(=O)C>[CH3:1][S:2]([O:6][CH:7]([C:11]1[CH:21]=[CH:20][C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[CH:13][CH:12]=1)[CH2:8][CH2:9][CH3:10])(=[O:4])=[O:3]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 67981039Ethyl 4-(1-hydroxybutyl)benzoate

Product 1

HCID 86667300HCID 86667300, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

Methanesulfonyl chloride (341 mg, 2.97 mmol) was added dropwise to a solution of ethyl 4-(1-hydroxybutyl)benzoate (504 mg, 2.27 mmol) and triethylamine (477 mg, 4.58 mmol) in dichloromethane (5 mL) at 0° C. The reaction was stirred at 0° C. for 2 hours. The reaction was diluted with ethyl acetate and washed with saturated ammonium chloride, saturated sodium bicarbonate, and brine. The organics were dried over sodium sulfate, filtered and concentrated to give ethyl 4-(1-(methylsulfonyloxy)butyl)benzoate. 1H NMR (400 MHz, CDCl3, δ): 8.02-8.10 (d, J=8.19 Hz, 2 H), 7.44 (d, J=8.19 Hz, 2 H), 5.50-5.61 (m, 1 H), 4.37 (q, J=7.22 Hz, 2 H), 1.97-2.11 (m, 1 H), 1.78-1.88 (m, 1 H), 1.39 (t, J=7.22 Hz, 3 H), 1.28-1.52 (m, 2 H), 0.94 (t, J=7.41 Hz, 3 H).

Workup

  1. washwashed with saturated ammonium chloride, saturated sodium bicarbonate, and brine
  2. dry with materialThe organics were dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-859ed4a6c8974c398b98104c9e9b6d53
Source dataset
uspto-grants-2014_08
Patent number
US08809342B2

Reaction notes

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