Ytterbium triflate → HCID 66823720, compound

HRID 879081Notes

Reaction equation

HRID 879081 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:17][CH2:16]2)=[C:11]([CH:18]2[C:20]3([C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[O:22][C:21]3([CH3:29])[CH3:28])[O:19]2)[CH:10]=1.[O-]S(C(F)(F)F)(=O)=O.[Yb+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O.Cl([O-])(=O)(=O)=O.[Li+]>C(OCC)C>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[CH2:17][CH2:16]2)=[C:11]([CH:18]2[C:24](=[O:25])[C:23]([CH3:27])([CH3:26])[O:22][C:21]([CH3:29])([CH3:28])[C:20]2=[O:19])[CH:10]=1

Participants

5

Reactant 3

HCID 2733225Ytterbium triflate2×HCID 23665649Lithium perchlorate2×HCID 86663673HCID 86663673, compound

Product 1

HCID 66823720HCID 66823720, compoundYield 15.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
27 °C

Procedure

To a mixture of 2-(2′,4′-dichloro-4-cyclopropylbiphenyl-3-yl)-4,4,6,6-tetramethyl-1,5-dioxa-spiro[2.4]heptan-7-one (17.80 g, 0.041 mol) and ytterbium triflate (2.20 g, 4.41 mmol) is added a solution of 5M lithium perchlorate (prepared from 42 ml diethyl ether and 22.30 g lithium perchlorate). The resulting suspension is stirred at room temperature for 17 days, at which stage further diethyl ether (42 ml), lithium perchlorate (22.3 g, 0.21 mol) and ytterbium triflate (19.8 g, 0.035 mol) is added. The reaction mixture is then heated at 27° C. (internal temperature) for 1 day, followed by partitioning between diethyl ether and distilled water. The two phases are separated, the aqueous phase is extracted with diethyl ether (×2), and then all organic fractions are combined, washed with brine then dried over magnesium sulphate. The suspension is filtered and the filtrate is concentrated in vacuo. The crude material is purified by flash column chromatography (ethyl acetate/hexane eluant) to give an oil which is triturated with hexanes to afford 4-(2′,4′-dichloro-4-cyclopropylbiphenyl-3-yl)-2,2,6,6-tetramethylpyran-3,5-dione (2.80 g) as a white solid.

Workup

  1. additionis added
  2. customby partitioning between diethyl ether
  3. distillationdistilled water
  4. customThe two phases are separated
  5. extractionthe aqueous phase is extracted with diethyl ether (×2)
  6. washwashed with brine
  7. dry with materialthen dried over magnesium sulphate
  8. filtrationThe suspension is filtered
  9. concentrationthe filtrate is concentrated in vacuo
  10. customThe crude material is purified by flash column chromatography (ethyl acetate/hexane eluant)
  11. customto give an oil which
  12. customis triturated with hexanes

Sources & evidence

ORD record
ord-61dab8b664094e27836bbb0ef49a7416
Source dataset
uspto-grants-2015_03
Patent number
US08987476B2

Reaction notes

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