Carbon Dioxide → HCID 68826125, compound

HRID 852402Notes

Reaction equation

HRID 852402 reaction equation
CC(C[AlH]CC(C)C)C.C(=O)=O.[F:13][C:14]([F:30])([F:29])[O:15][C:16]1[CH:21]=[CH:20][C:19]([C:22]#[C:23][CH2:24][CH2:25][C:26](=[O:28])[CH3:27])=[CH:18][CH:17]=1.OS([O-])(=O)=O.[K+]>C1COCC1>[F:13][C:14]([F:29])([F:30])[O:15][C:16]1[CH:17]=[CH:18][C:19]([C:22]#[C:23][CH2:24][CH2:25][CH:26]([OH:28])[CH3:27])=[CH:20][CH:21]=1

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 14487Diisobutylaluminum hydrideHCID 516920Potassium bisulfateHCID 68823916HCID 68823916, compound

Product 1

HCID 68826125HCID 68826125, compoundYield 105.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Within 15 min was dropped 1.46 ml (1.2 M in toluene, 1.75 mmol) of DIBAL-H to a dry ice cooled (−30° C.) solution of 0.23 g (0.88 mmol) 6-(4-trifluoromethoxy-phenyl)-hex-5-yn-2-one in 4 ml of THF. The reaction was warmed up (0° C. for 1 h 10 min) and neutralized with aqueous 10% KHSO4 solution. The mixture was extracted with ether (three times), the organic phases were washed with a aqueous 10% NaCl solution, dried (Na2SO4) and evaporated to give 0.24 g of the title compound as light brown oil.

Workup

  1. extractionThe mixture was extracted with ether (three times)
  2. washthe organic phases were washed with a aqueous 10% NaCl solution
  3. dry with materialdried (Na2SO4)
  4. customevaporated

Sources & evidence

ORD record
ord-45472b325b314324aa0113fffbc1db61
Source dataset
uspto-grants-2007_08
Patent number
US07253192B2

Reaction notes

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