Triethylamine → HCID 86667300, compound

HRID 1427457Notes

Reaction equation

HRID 1427457 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, 2H), 7.44 (d, J=8.19 Hz, 2H), 5.50-5.61 (m, 1H), 4.37 (q, J=7.22 Hz, 2H), 1.97-2.11 (m, 1H), 1.78-1.88 (m, 1H), 1.39 (t, J=7.22 Hz, 3H), 1.28-1.52 (m, 2H), 0.94 (t, J=7.41 Hz, 3H).

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-f7a25270f5a74104b5a883ef379b4109
Source dataset
uspto-grants-2015_01
Patent number
US08933104B2

Reaction notes

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