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

HRID 1677
Notes
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Reaction equation

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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 102793rel-(1R,2S)-2-PhenylcyclohexanolHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 12532676Methyl 4-hydroxy-2-methoxybenzoate

Product 1

HCID 22883080Methyl 4-(cis-2-phenyl-1-cyclohexanoyloxy)-2-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

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

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

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes