Potassium Phosphate, Tribasic → 2-[6-(3-Adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl]-3-hydroxy-cyclopent-2-enone

HRID 2377224Notes

Reaction equation

HRID 2377224 reaction equation
[C:1]1(=[O:7])[CH2:5][CH2:4][C:3](=[O:6])[CH2:2]1.[C:8]12([C:18]3[CH:19]=[C:20]([C:26]4[CH:27]=[C:28]5[C:33](=[CH:34][CH:35]=4)[CH:32]=[C:31](OS(C4C=CC(C)=CC=4)(=O)=O)[CH:30]=[CH:29]5)[CH:21]=[CH:22][C:23]=3[O:24][CH3:25])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC([O-])=O.CC([O-])=O.[Pd+2]>[C:8]12([C:18]3[CH:19]=[C:20]([C:26]4[CH:27]=[C:28]5[C:33](=[CH:34][CH:35]=4)[CH:32]=[C:31]([C:2]4[C:1](=[O:7])[CH2:5][CH2:4][C:3]=4[OH:6])[CH:30]=[CH:29]5)[CH:21]=[CH:22][C:23]=3[O:24][CH3:25])[CH2:17][CH:12]3[CH2:13][CH:14]([CH2:16][CH:10]([CH2:11]3)[CH2:9]1)[CH2:15]2

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 774661,3-CyclopentanedioneHCID 59856317Toluene-4-sulfonic acid 6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl ester

Product 1

HCID 116626852-[6-(3-Adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl]-3-hydroxy-cyclopent-2-enone

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

A flame-dried Schlenk tube containing a Teflon coated stir bar was charged with Pd(OAc)2 (20 mg, 0.088 mmol), (2-dicyclohexylphosphino)-2′,4′,6′-triisopropyl biphenyl (105 mg, 0.22 mmol), 1,3-cyclopentanedione (65 mg, 0.66 mmol), toluene-4-sulfonic acid 6-(3-adamantan-1-yl-4-methoxyphenyl)-naphthalen-2-yl ester (238 mg, 0.44 mmol) and finely ground K3PO4 (233 mg, 1.1 mmol). The tube was capped with a septum, evacuated and backfilled with nitrogen three times, 2 mL of dry dioxane was injected and the mixture was heated to 100° C. for 3 h. The mixture was then cooled, diluted with EtOAc, washed with 1N HCl, dried over Na2SO4 and filtered. The filtrate was concentrated and purified by flash chromatography using MeOH—CH2Cl2.

Workup

  1. additionA flame-dried Schlenk tube containing a Teflon coated stir bar
  2. customThe tube was capped with a septum
  3. customevacuated
  4. temperatureThe mixture was then cooled
  5. additiondiluted with EtOAc
  6. washwashed with 1N HCl
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationThe filtrate was concentrated
  10. custompurified by flash chromatography

Sources & evidence

ORD record
ord-9de3f3322bac47eb9516a5bce21cea26
Source dataset
uspto-grants-2008_12
Patent number
US07468462B2

Reaction notes

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