Water → 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propyl methanesulfonate

HRID 322306Notes

Reaction equation

HRID 322306 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[C:6]1(/[CH:12]=[CH:13]/[C:14]2[O:15][CH:16]=[C:17]([CH2:19][S:20][C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH2:29][OH:30])=[CH:23][CH:22]=3)[N:18]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.C(N(CC)CC)C.O>O1CCCC1>[CH3:1][S:2]([O:30][CH2:29][CH2:28][CH2:27][C:24]1[CH:23]=[CH:22][C:21]([S:20][CH2:19][C:17]2[N:18]=[C:14](/[CH:13]=[CH:12]/[C:6]3[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:15][CH:16]=2)=[CH:26][CH:25]=1)(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 220096833-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propanol

Product 1

HCID 220098243-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propyl methanesulfonateYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methanesulfonyl chloride (320 mg) was added to a solution of 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propanol (500 mg) and triethylamine (280 mg) in tetrahydrofuran (30 ml) at 0° C. and then stirred for 4 hours at room temperature. To the reaction mixture was added water, and extracted with ethyl acetate. The ethyl acetate layer was washed with water, dried (MgSO4), and concentrated under reduced pressure to give 3-[4-[2-[(E)-2-phenylethenyl]-4-oxazolylmethylthio]phenyl]propyl methanesulfonate (540 mg, 90%). Recrystallization from ethyl acetate-hexane gave pale yellow prisms, mp 97-98° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with water
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-543d06d20adb4bfaa4ae166e79fbe08a
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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