Triphenylphosphine → Methyl 4-(4-tetrahydropyranoyloxy)-2-methoxy-benzoate

HRID 1674

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.[O:33]1[CH2:38][CH2:37][CH:36](O)[CH2:35][CH2:34]1.N(C(OCC)=O)=N[C:42](OCC)=[O:43]>C1COCC1>[O:33]1[CH2:38][CH2:37][CH:36]([C:42]([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:43])[CH2:35][CH2:34]1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (713 mg, 3.92 mmol) in dry THF (7.5 mL) was added triphenylphosphine (1.42 g, 5.4 mmol) and the solution was cooled to 0° C. A 2.5 mL volume of tetrahydro-4H-pyran-4-ol (466 mL, 4.90 mmol) and diethyl azodicarboxylate (850 μL, 5.4 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-tetra-hydropyranoyloxy)-2-methoxy-benzoate.

Workup

filtrationThe reaction was filtered
customthe solvent was removed under reduced pressure
customThe residue was chromatographed on a silica gel column
washEtOAc and eluted with same
customthe solvent removed under reduced pressure

Sources & evidence

ORD record: ord-2e02459c44114d51802676f652203008
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726172

Linked notes

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