Tetrahydrofuran → Methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate

HRID 1697

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HRID 1697 반응식
[OH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[S:33](=[C:36]1[CH:41]=C(O)C=CO1)(=[O:35])=[O:34].N(C(OCC)=O)=NC(OCC)=[O:46].[CH2:55]1[CH2:59][O:58][CH2:57][CH2:56]1>>[S:33](=[C:36]1[CH:55]=[CH:59][O:58][C:57]([C:56]([O:1][C:2]2[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=2)=[O:46])=[CH:41]1)(=[O:35])=[O:34]

참가 물질

6

반응물 5

HCID 8028Tetrahydrofuran2회HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoateHCID 19690976Sulfonylpyran-4-ol

생성물 1

HCID 86752226Methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate

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온도
0 °C

실험 절차

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (364 mg, 2.0 mmol) in dry THF (4 mL) was added triphenylphosphine (524.6 mg, 2.0 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of sulfonylpyran-4-ol (200 mg, 1.33 mmol) and diethyl azodicarboxylate (315 μL, 2.0 mmol) in THF was added dropwise via addition funnel over 0.5 h. The reaction was filtered and the solvent was removed under reduced pressure. The residue was chromatographed on a silica gel column packed in 60:40 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-[4-sulfonylpyranoyloxy]-2-methoxybenzoate.

후처리

  1. filtrationThe reaction was filtered
  2. customthe solvent was removed under reduced pressure
  3. customThe residue was chromatographed on a silica gel column
  4. washEtOAc and eluted with same
  5. customthe solvent removed under reduced pressure

출처 및 근거

ORD 기록
ord-e3ff06e7d5dc4790a4038ff5d1f041f4
출처 데이터셋
uspto-grants-1998_03
특허 번호
US05726172

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