Sodium Carbonate → HCID 59853021, compound

HRID 1670253Notes

Reaction equation

HRID 1670253 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:17])([CH3:16])[CH3:15])[CH2:7][CH:6]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C([O-])([O-])=O.[Na+].[Na+]>C1COCC1>[C:4]([C:5]1[CH2:10][CH2:9][CH:8]([NH:11][C:12](=[O:18])[O:13][C:14]([CH3:16])([CH3:15])[CH3:17])[CH2:7][CH:6]=1)#[CH:3]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 2724141Tetrabutylammonium FluorideHCID 59853030HCID 59853030, compound

Product 1

HCID 59853021HCID 59853021, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of tert-butyl 4-(2-(trimethylsilyl)ethynyl)cyclohex-3-enylcarbamate (112 mg, 0.38 mmol) in THF was cooled to −15° C., treated with 1.0 M tetrabutylammonium fluoride in THF (Aldrich, 440 μL, 0.44 mmol) and the mixture stirred at −15° C. for 40 min. The mixture was treated with 5% Na2CO3 (25 mL) and extracted with ether. The ether extract was washed with 5% Na2CO3 and brine, dried (MgSO4) and concentrated in vacuo to give the title compound (83 mg, 99%) as a brown oil. 1H NMR (DMSO-d6) δ 6.09 (s, 1H), 4.51 (s, 1H), 3.77 (s, 1H), 2.82 (s, 1H), 2.47 (d, 1H, J=18.3 Hz), 2.35-2.16 (m, 2H), 2.04-1.79 (m, 2H), 1.72-1.51 (m, 1H), 1.43 (s, 9H).

Workup

  1. extractionextracted with ether
  2. extractionThe ether extract
  3. washwas washed with 5% Na2CO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4a71ff6481d0478783141d261c236cee
Source dataset
uspto-grants-2011_08
Patent number
US07989477B2

Reaction notes

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