Water → 4-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl methanesulfonate

HRID 440469Notes

Reaction equation

HRID 440469 reaction equation
C(N(CC)CC)C.[O:8]1[CH2:13][CH2:12][CH2:11][CH2:10][CH:9]1[O:14][CH2:15][CH2:16][C:17]1[CH:25]=[CH:24][C:20]([CH2:21][CH2:22][OH:23])=[CH:19][CH:18]=1.[CH3:26][S:27](Cl)(=[O:29])=[O:28].O>C(Cl)Cl>[CH3:26][S:27]([O:23][CH2:22][CH2:21][C:20]1[CH:19]=[CH:18][C:17]([CH2:16][CH2:15][O:14][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][O:8]2)=[CH:25][CH:24]=1)(=[O:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 542369074-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol

Product 1

HCID 224075944-(2-(Tetrahydropyran-2-yloxy)ethyl)phenethyl methanesulfonateYield 99.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (3.22 g, 31.82 mmol) was added to a solution of 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethyl alcohol (4.00 g, 15.97 mmol) in methylene chloride (40 ml). The mixture was stirred under ice-cooling, and methanesulfonyl chloride (2.19 g, 19.11 mmol) was added dropwise to the mixture. After the addition, the resulting mixture was stirred under ice-cooling for 10 minutes. Then, water (40 ml) was added. The mixture was extracted with methylene chloride and dried over magnesium sulfate. Evaporation of the solvent gave the desired 4-(2-(tetrahydropyran-2-yloxy)ethyl)phenethyl methanesulfonate (5.24 g, 99%).

Workup

  1. temperaturecooling
  2. additionAfter the addition
  3. stirringthe resulting mixture was stirred under ice-
  4. temperaturecooling for 10 minutes
  5. extractionThe mixture was extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. customEvaporation of the solvent

Sources & evidence

ORD record
ord-5981e944546a49d4847d6ab1f211e83c
Source dataset
uspto-grants-1996_05
Patent number
US05519139

Reaction notes

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