Carbon Dioxide → HCID 68826125, compound

HRID 751238Notes

Reaction equation

HRID 751238 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, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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

Workup

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

Sources & evidence

ORD record
ord-0458bbe6d5344ac6a776c935eab8079b
Source dataset
uspto-grants-2008_07
Patent number
US07405236B2

Reaction notes

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