Dimethyl Sulfoxide → HCID 18677155, compound

HRID 1634125Notes

Reaction equation

HRID 1634125 reaction equation
C(Cl)(C(Cl)=O)=O.CS(C)=O.[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[C:18][CH:19]([OH:22])[CH2:20][CH3:21])[CH:12]=1.C(N(CC)CC)C>C(Cl)Cl.O>[N:11]1[CH:16]=[CH:15][CH:14]=[C:13]([C:17]#[C:18][C:19](=[O:22])[CH2:20][CH3:21])[CH:12]=1

Participants

7

Reactant 4

HCID 679Dimethyl SulfoxideHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 18677128HCID 18677128, compound

Product 1

HCID 18677155HCID 18677155, compoundYield 101.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-78 °C

Procedure

To a solution of (COCl)2 (7.9 mL, 91.0 mmol) in CH2Cl2 (300 mL) was added DMSO (11.0 mL, 151 mmol) at −78° C., followed by 1-(3-pyridinyl)-1-pentyn-3-ol (12.2 g, 75.6 mmol) in CH2Cl2 (100 mL). The mixture was stirred at −78° C. for 1 hr, and then quenched with triethylamine (32 mL, 227 mmol). After being warmed to 0° C., the mixture was diluted with water and the layers were separated. The organic phase was dried over MgSO4 and concentrated to give 1(3-pyridinyl)-1-pentyn-3-one (12.2 g, 99%) as an oil. 1H NMR (CDCl3, 400 MHz) 8.81 (bs, 1H), 8.68 (bs, 1H), 7.87 (m, 1H), 7.32 (m, 1H), 2.73 (q, J=7.4Hz, 2H), 1.24 (t, J=7.4 Hz, 3H).

Workup

  1. temperatureAfter being warmed to 0° C.
  2. customthe layers were separated
  3. dry with materialThe organic phase was dried over MgSO4
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-0c01179df8ef46ffa546d43b2a81bc49
Source dataset
uspto-grants-2003_01
Patent number
US06506747B1

Reaction notes

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