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2-Methyl-2-butene → (Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acid

HRID 1458317
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HRID 1458317 반응식
[C:1]([O:4][CH2:5]/[C:6](/[C:16]1[CH:21]=[CH:20][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:18][CH:17]=1)=[C:7](/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)\[CH:8]=[O:9])(=[O:3])[CH3:2].CC(=CC)C.[O-:31]Cl=O.[Na+]>CC(O)(C)C.O>[C:1]([O:4][CH2:5]/[C:6](/[C:16]1[CH:17]=[CH:18][C:19]([S:22]([CH3:25])(=[O:24])=[O:23])=[CH:20][CH:21]=1)=[C:7](/[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)\[C:8]([OH:31])=[O:9])(=[O:3])[CH3:2]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

6

반응물 3

HCID 105532-Methyl-2-buteneHCID 23668197Sodium ChloriteHCID 86753445(Z)-4-Acetoxy-3-(4-(Methylsulfonyl)Phenyl)-2-Phenyl-2-Butenal

생성물 1

HCID 11617716(Z)-4-Acetoxy-3-(4-(methylsulfonyl) phenyl)-2-phenylbut-2-enoic acid수율 89.7%

시약·촉매·용매 2

HCID 962Water용매
HCID 6386
tert-Butanol
용매

실험 절차

To a solution of the aldehyde from Example 3 (160 mg) and 2-methyl-2-butene (6 mL) in 2-methyl-2-propanol (35 mL) was added a solution of NaClO2 (1 g) and NaH2PO4 (1 g) in 10 mL of H2O. The mixture was stirred for 2 h at r.t., and concentrated. The residue was then taken into 50 mL of pH 7 buffer solution (1M) and extracted with EtOAc (50 mL). The extract was dried over MgSO4 and concentrated. The residue was purified by flash chromatography, eluting with 3:1 EtOAc/hexane containing 1% HOAc to give 150 mg of the title compound as a white solid.

후처리

  1. concentrationconcentrated
  2. extractionextracted with EtOAc (50 mL)
  3. dry with materialThe extract was dried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was purified by flash chromatography
  6. washeluting with 3:1 EtOAc/hexane containing 1% HOAc

출처 및 근거

ORD 기록
ord-30fb426d7eb843a6b2e46158176bb47e
출처 데이터셋
uspto-grants-1998_12
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05849943

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