Trifluoromethanesulfonic anhydride → HCID 86758573, compound

HRID 991870Notes

Reaction equation

HRID 991870 reaction equation
[F:1][C:2]([F:15])([F:14])[S:3]([O:6]S(C(F)(F)F)(=O)=O)(=[O:5])=[O:4].[CH3:16][C:17]1([CH3:43])[CH2:22][CH2:21][CH2:20][C:19](=O)[CH:18]1/[CH:24]=[CH:25]/[C:26]#[C:27][C:28]1[CH:42]=[CH:41][C:31]([C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:40])([CH3:39])[CH3:38])=[O:33])=[CH:30][CH:29]=1.C(C1C=C(C)C=C(C(C)(C)C)N=1)(C)(C)C>ClCCl.C(OCC)(=O)C>[CH3:16][C:17]1([CH3:43])[C:18](/[CH:24]=[CH:25]/[C:26]#[C:27][C:28]2[CH:29]=[CH:30][C:31]([C:32]([O:34][CH2:35][CH2:36][Si:37]([CH3:38])([CH3:40])[CH3:39])=[O:33])=[CH:41][CH:42]=2)=[C:19]([O:6][S:3]([C:2]([F:15])([F:14])[F:1])(=[O:5])=[O:4])[CH2:20][CH2:21][CH2:22]1

Participants

6

Reactant 3

HCID 67749Trifluoromethanesulfonic anhydrideHCID 988982,6-Di-tert-butyl-4-methylpyridineHCID 86758572HCID 86758572, compound2×

Product 1

HCID 86758573HCID 86758573, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

Trifluoromethanesulfonic anhydride (0.109 mL, 0.65 mmol) was added to a solution of (trimethylsilyl)ethyl (±)-(E)-4-(4-(2,2-dimethyl-6-oxocyclohexyl)but-3-en-1-ynyl)benzoate (Compound G, 150 mg, 0.38 mmol) and 2,6-di-tert-butyl-4-methylpyridine (DBMP, 218 mg, 1.06 mmol) in dichloromethane (4 mL). The flask was sealed with a plastic cap and stirred for 2 days at room temperature. The solution was diluted with ethyl acetate and washed with 10% aqueous H3PO4. The layers were separated and the aqueous layer extracted three times with ethyl acetate. The combined organic layers were washed with 5% aqueous NaHCO3, and brine, and dried (Na2SO4). The solvents were removed under reduced pressure, and the residue was purified by silica gel chromatography (10:1, hexane:ethyl acetate) to give the title compounds as a 1:1 mixture of isomers. The compounds were separated by HPLC using a Whatman Partisil-10 1×50 cm column (95:5, hexane:ethyl acetate) to provide the title compound as a colorless oil:

Workup

  1. customThe flask was sealed with
  2. customa plastic cap
  3. washwashed with 10% aqueous H3PO4
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted three times with ethyl acetate
  6. washThe combined organic layers were washed with 5% aqueous NaHCO3, and brine
  7. dry with materialdried (Na2SO4)
  8. customThe solvents were removed under reduced pressure
  9. customthe residue was purified by silica gel chromatography (10:1, hexane:ethyl acetate)

Sources & evidence

ORD record
ord-3d4b9e8ef1d041cabed4e47bc198cf65
Source dataset
uspto-grants-2002_10
Patent number
US06465646B1

Reaction notes

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