Tetrahydrofuran → HCID 59853030, compound

HRID 1670252Notes

Reaction equation

HRID 1670252 reaction equation
FC(F)(F)S(OC1CCC(C([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=O)CC=1)(=O)=O.[CH3:22][Si:23]([C:26]#[CH:27])([CH3:25])[CH3:24].CC[N:30]([CH2:33][CH3:34])[CH2:31]C.[CH2:35]1[CH2:39]O[CH2:37][CH2:36]1.CC[O:42]C(C)=O>[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH3:22][Si:23]([CH3:25])([CH3:24])[C:26]#[C:27][C:35]1[CH2:39][CH2:34][CH:33]([NH:30][C:31](=[O:42])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])[CH2:37][CH:36]=1

Participants

8

Reactant 5

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 66111TrimethylsilylacetyleneHCID 60209246HCID 60209246, compound

Product 1

HCID 59853030HCID 59853030, compoundYield 81%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 178418397HCID 178418397, compoundCatalyst

Procedure

A mixture of 4-(tert-butoxycarbonyl)cyclohex-1-enyl trifluoromethanesulfonate (170 mg, 0.49 mmol), trimethylsilylacetylene (138 μL, 0.98 mmol), Et3N (0.68 mL) and THF (8 mL) in a reaction flask was purged with argon and treated in turn with CuI (14 mg, 0.072 mmol) and (Ph3P)4Pd (27 mg, 0.024 mmol). The reaction mixture was stirred at room temperature for 25 min, and then diluted with EtOAc (50 mL), washed with saturated aq. NaHCO3 solution and brine, dried (MgSO4) and concentrated in vacuo. The crude product was purified by flash chromatography on SiO2 eluting with 0-25% EtOAc/hexanes to give the title compound (116 mg, 81%) as a yellow solid. 1H NMR (DMSO-d6) δ 6.06 (s, 1H), 4.50 (s, 1H), 3.76 (s, 1H), 2.46 (d, 1H, J=18.8 Hz), 2.36-2.14 (m, 2H), 2.00-1.78 (m, 2H), 1.66-1.50 (m, 1H), 1.43 (s, 9H), 0.27-0.05 (m, 9H).

Workup

  1. customwas purged with argon
  2. washwashed with saturated aq. NaHCO3 solution and brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe crude product was purified by flash chromatography on SiO2 eluting with 0-25% EtOAc/hexanes

Sources & evidence

ORD record
ord-b43b64b9521547f5bbc2da78f02c852e
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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