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

HRID 1697

Reaction equation

HRID 1697 reaction equation
[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]

Participants

6

Reactant 5

HCID 8028Tetrahydrofuran2×HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoateHCID 19690976Sulfonylpyran-4-ol

Product 1

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

Conditions

Temperature
0 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-e3ff06e7d5dc4790a4038ff5d1f041f4
Source dataset
uspto-grants-1998_03
Patent number
US05726172

Linked notes

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