Triethylamine → HCID 86601925, compound

HRID 2112014Notes

Reaction equation

HRID 2112014 reaction equation
[OH:1][C:2]1[CH:28]=[CH:27][C:5]([O:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[O:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:36][S:37](Cl)(=[O:39])=[O:38]>ClCCl>[CH3:36][S:37]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH2:7][CH2:8][C:9]2[CH:10]=[C:11]([CH:24]=[CH:25][CH:26]=2)[O:12][CH2:13][C:14]2[CH:23]=[CH:22][CH:21]=[CH:20][C:15]=2[C:16]([O:18][CH3:19])=[O:17])=[CH:27][CH:28]=1)(=[O:39])=[O:38]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 68868795HCID 68868795, compound

Product 1

HCID 86601925HCID 86601925, compoundYield 95.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-20 °C

Procedure

Methyl 2-({3-[2-(4-hydroxyphenoxy)ethyl]phenoxy}methyl)benzoate (0.096 g, 0.25 mmol) was dissolved in dichloromethane (10 ml) and cooled to −20° C. Triethylamine (0.039 g, 0.38 mmol) was added drop wise and methanesulfonyl chloride (0.032 g, 0.28 mmol) was added drop wise. The ice bath was removed and the mixture was wormed to room temperature. Add diethyleter (5 ml) and filter of the precipitate, wash the organic phase with two portions of brine (5 ml) and dry (MgSO4). Removing the solvent by evaporation gave 0.109 gram of methyl 2-{[3-(2-{4-[(methylsulfonyl)oxy]phenoxy}ethyl)-phenoxy]methyl}benzoate (yield 94.1%).

Workup

  1. customThe ice bath was removed
  2. customwas wormed to room temperature
  3. additionAdd diethyleter (5 ml)
  4. filtrationfilter of the precipitate
  5. washwash the organic phase with two portions of brine (5 ml)
  6. dry with materialdry (MgSO4)
  7. customRemoving the solvent
  8. customby evaporation

Sources & evidence

ORD record
ord-154e56dc054446849fd4df7d95045acd
Source dataset
uspto-grants-2009_04
Patent number
US07521461B2

Reaction notes

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