Dimethylformamide → HCID 85825730, compound

HRID 250536Notes

Reaction equation

HRID 250536 reaction equation
[CH3:1][C:2]([OH:10])([CH2:5][CH2:6][CH:7](C)C)[C:3]#[CH:4].CN(C=O)C.[CH3:16]CN(CC)CC.FC(F)(F)S(O[Si:29]([C:32]([CH3:35])([CH3:34])[CH3:33])([CH3:31])[CH3:30])(=O)=O>CCOC(C)=O>[C:32]([Si:29]([O:10][C:2]([CH2:5][CH:6]([CH3:7])[CH3:16])([CH3:1])[C:3]#[CH:4])([CH3:31])[CH3:30])([CH3:35])([CH3:34])[CH3:33]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 891823,6-Dimethyl-1-heptyn-3-olHCID 123564tert-Butyldimethylsilyl trifluoromethanesulphonate

Product 1

HCID 85825730HCID 85825730, compoundYield 106.9%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

An oven-dried flask was charged with 3,6-dimethyl-1-heptyn-3-ol (1.0 g, 0.007 mol) and dry DMF (7.0 mL). To this solution, cooled in an ice bath, was added Et3N (3.6 mL, 0.025 mol) followed by dropwise addition of tert-butyldimethylsilyl trifluoromethanesulfonate (2.5 g, 0.014 mol) under nitrogen atmosphere. The resulting mixture was stirred at RT for 18 h and then diluted with EtOAc (80 mL). The organic layer was washed with saturated solution of NH4Cl (30 mL), water (4×20 mL), brine (40 mL), dried over sodium sulfate, and evaporated to afford the desired compound (1.8 g), as a yellow oil, used in the next step without further purification. Rf 0.9 (EtOAc/hexanes 1/9); 1H NMR (CDCl3) δ 0.15 (s, 6H), 0.88-0.84 (m, 15H), 1.38-1.29 (m, 1H), 1.42 (s, 3H), 1.54-1.48 (m, 2H), 1.62-1.55 (m, 2H), 2.38 (s, 1H).

Workup

  1. temperatureTo this solution, cooled in an ice bath
  2. washThe organic layer was washed with saturated solution of NH4Cl (30 mL), water (4×20 mL), brine (40 mL)
  3. dry with materialdried over sodium sulfate
  4. customevaporated

Sources & evidence

ORD record
ord-87edf042a37940eebc2f3b11d1bae00f
Source dataset
uspto-grants-2011_01
Patent number
US07863312B2

Reaction notes

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