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

HRID 322306ノート

反応式

HRID 322306 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-543d06d20adb4bfaa4ae166e79fbe08a
出典データセット
uspto-grants-2001_04
特許番号
US06211215B1

反応ノート

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