Hydrochloric Acid → (E)-S-phenyl 3-(4-hydroxy-3,5-dimethylstyryl)benzothioate

HRID 2368869ノート

反応式

HRID 2368869 の反応式
COC[O:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=2)[C:14](=[O:22])[S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][C:6]=1[CH3:29].Cl>CC(O)C.C1COCC1>[OH:4][C:5]1[C:27]([CH3:28])=[CH:26][C:8](/[CH:9]=[CH:10]/[C:11]2[CH:12]=[C:13]([CH:23]=[CH:24][CH:25]=2)[C:14](=[O:22])[S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:7][C:6]=1[CH3:29]

参加物

5

反応物 2

HCID 313Hydrochloric AcidHCID 86672878(E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate

生成物 1

HCID 44472868(E)-S-phenyl 3-(4-hydroxy-3,5-dimethylstyryl)benzothioate

試薬・触媒・溶媒 2

HCID 3776Isopropanol溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of (E)-S-phenyl 3-(4-(methoxymethoxy)-3,5-dimethylstyryl)benzothioate (80 mg, 0.198 mmol) in i-PrOH and THF (½ mL) was added 0.5 mL of concentrated HCl. The reaction mixture was stirred overnight (about 18 hours). After removal of solvent under reduced pressure, the residue was dissolved in EtOAc. The solution was washed with 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-hydroxy-3,5-dimethylstyryl)-benzothioate in quantitative yield. Azo-linked compounds of Formula I are prepared following usual syntheses for preparing aromatic or heteroaromatic azo compounds. A typical scheme is shown in Scheme 3.

後処理

  1. customAfter removal of solvent under reduced pressure
  2. dissolutionthe residue was dissolved in EtOAc
  3. washThe solution was washed with brine
  4. dry with materialdried with Na2SO4
  5. filtrationThe solution was filtered
  6. concentrationconcentrated
  7. customThe compound was purified by column chromatography (9:1 Hexane:EtOAc)

出典と根拠

ORDレコード
ord-50e3cb7fcd494b169b23484252a2f418
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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