Triphenylphosphine → Methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

HRID 1677

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.[C:33]1([C@@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2O)[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1.N(C(OCC)=O)=N[C:48](OCC)=[O:49]>C1COCC1>[C:33]1([C@H:39]2[CH2:44][CH2:43][CH2:42][CH2:41][C@H:40]2[C:48]([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:49])[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a stirred solution of methyl 4-hydroxy-2-methoxybenzoate (310 mg, 1.7 mmol) in dry THF (1.25 mL) was added triphenylphosphine (446 mg, 1.7 mmol) and the solution was cooled to 0° C. A 500 mL volume of trans-2-phenyl-1-cyclohexanol (200 mg, 1.35 mmol) and diethyl azodicarboxylate (319 μL, 2.02 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 92:8 hexanes:EtOAc and eluted with same. The appropriate fractions were combined and the solvent removed under reduced pressure to afford methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate.

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-e05a7f6ef00b40218847ea8339f5616a
Source dataset: uspto-grants-1998_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05726172

Linked notes

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