Propargyl bromide → HCID 59463772, compound

HRID 1713349Notes

Reaction equation

HRID 1713349 reaction equation
[Al].[CH2:2](Br)[C:3]#[CH:4].[F:6][C:7]([F:27])([F:26])[C:8](=[O:25])[CH2:9][C:10]1([CH3:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([S:20]([CH3:23])(=[O:22])=[O:21])[CH:18]=2)[O:13][CH2:12][CH2:11]1>C1COCC1.C1(C)C=CC=CC=1>[F:27][C:7]([F:6])([F:26])[C:8]([CH2:9][C:10]1([CH3:24])[C:19]2[C:14](=[CH:15][CH:16]=[C:17]([S:20]([CH3:23])(=[O:21])=[O:22])[CH:18]=2)[O:13][CH2:12][CH2:11]1)([OH:25])[CH2:4][C:3]#[CH:2]

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 5359268AluminumHCID 59463775HCID 59463775, compound

Product 1

HCID 59463772HCID 59463772, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
40 °C

Procedure

A mixture of 70 mg (2.75 mmol) of aluminum foil and 0.8 mg (0.003 mmol) of mercuric chloride in 3 mL of anhydrous THF was vigorously stirred. After 20 minutes, 0.31 mL (2.75 mmol) of a 80% solution of propargyl bromide in toluene was added and the reaction was warmed at 40° C. for one hour. The dark grey solution was then added to a chilled (0° C.) solution of 300 mg (0.88 mmol) of 1,1,1-trifluoro-3-(6-methanesulfonyl-4-methylchroman-4-yl)propan-2-one in 10 mL of dry tetrahydrofuran. The reaction was warmed to room temperature overnight, concentrated in vacuo, quenched with ice and extracted with diethyl ether. The combined organic fractions were dried over magnesium sulfate, filtered and concentrated in vacuo to afford 330 mg of crude 1,1,1-trifluoro-2-(6-methanesulfonyl-4-methylchroman-4-ylmethyl)pent-4-yn-2-ol as an oil.

Workup

  1. additionThe dark grey solution was then added to
  2. temperatureThe reaction was warmed to room temperature overnight
  3. concentrationconcentrated in vacuo
  4. customquenched with ice
  5. extractionextracted with diethyl ether
  6. dry with materialThe combined organic fractions were dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-b359fd9025374f87a3b26028eb4d53c3
Source dataset
uspto-grants-2010_09
Patent number
US07795272B2

Reaction notes

Loading…