Thiophenol → (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

HRID 2368868ノート

反応式

HRID 2368868 の反応式
[CH3:1][O:2][CH2:3][O:4][C:5]1[C:21]([CH3:22])=[CH:20][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14]([OH:16])=O)=[CH:7][C:6]=1[CH3:23].C1CCC(N=C=NC2CCCCC2)CC1.[C:39]1([SH:45])[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=1>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:1][O:2][CH2:3][O:4][C:5]1[C:6]([CH3:23])=[CH:7][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](=[O:16])[S:45][C:39]2[CH:44]=[CH:43][CH:42]=[CH:41][CH:40]=2)=[CH:20][C:21]=1[CH3:22]

参加物

6

反応物 3

HCID 7969ThiophenolHCID 10868DicyclohexylcarbodiimideHCID 67262065(E)-3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzoic acid

生成物 1

HCID 86672878(E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

To a solution of (E)-3-[4-(methoxymethoxy)-3,5-dimethylstyryl]benzoic acid (0.1 g, 0.320 mmol) in DCM (5 mL) were added DCC (72.6 mg, 0.352 mmol), DMAP (7.9 mg, 0.064 mmol), and benzenethiol (65.7 μL, 0.640 mmol) at room temperature. The reaction mixture was stirred overnight (about 18 hours) and filtered through Celite. The filtrate was washed with 10% citric acid, brine, and dried with Na2SO4. The solution was filtered and concentrated. The compound was purified by column chromatography (9:1 Hexane:EtOAc) to afford (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate in quantitative yield.

後処理

  1. filtrationfiltered through Celite
  2. washThe filtrate was washed with 10% citric acid, brine
  3. dry with materialdried with Na2SO4
  4. filtrationThe solution was filtered
  5. concentrationconcentrated
  6. customThe compound was purified by column chromatography (9:1 Hexane:EtOAc)

出典と根拠

ORDレコード
ord-208e80c956a5438cb63a2877faf503d5
出典データセット
uspto-grants-2014_04
特許番号
US08703815B2

反応ノート

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