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

HRID 2368869노트

반응식

HRID 2368869 반응식
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]

참가 물질

5

반응물 2

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

생성물 1

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

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-50e3cb7fcd494b169b23484252a2f418
출처 데이터셋
uspto-grants-2014_04
특허 번호
US08703815B2

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