Tetrahydrofuran → HCID 60026398, compound

HRID 400661Notes

Reaction equation

HRID 400661 reaction equation
[F:1][C:2]([F:23])([F:22])[C:3](=[O:21])[CH2:4][C:5]([C:8]1[C:16]2[O:15][CH2:14][CH2:13][C:12]=2[CH:11]=[C:10]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:9]=1)([CH3:7])[CH3:6].[CH2:24]1[CH2:28]OC[CH2:25]1>C(OCC)C>[CH3:20][S:17]([C:10]1[CH:9]=[C:8]([C:5]([CH3:7])([CH3:6])[CH2:4][C:3]([C:2]([F:1])([F:22])[F:23])([OH:21])[CH2:28][C:24]#[CH:25])[C:16]2[O:15][CH2:14][CH2:13][C:12]=2[CH:11]=1)(=[O:18])=[O:19]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 60026401HCID 60026401, compound

Product 1

HCID 60026398HCID 60026398, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 1,1,1-trifluoro-4-(5-methanesulfonyl-2,3-dihydrobenzofuran-7-yl)-4-methylpentan-2-one (5.4 g, 15.4 mmol) in a mixture of 10 mL of anhydrous diethyl ether and 10 mL of anhydrous THF was treated with the organoaluminum reagent at −78° C. After 1 hour at −78° C. and 1 hour at room temperature, the reaction mixture was quenched with saturated ammonium chloride solution and diluted with water. The aqueous layer was extracted with three 100 mL portions of ethyl acetate. The combined organic layers were washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo to give 6.3 g of the title product as a solid, which was used without further purification (quantitative yield).

Workup

  1. custom1 hour at room temperature, the reaction mixture was quenched with saturated ammonium chloride solution
  2. additiondiluted with water
  3. extractionThe aqueous layer was extracted with three 100 mL portions of ethyl acetate
  4. washThe combined organic layers were washed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-36904e6712344460abe97a9df718108d
Source dataset
uspto-grants-2014_06
Patent number
US08741897B2

Reaction notes

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