Ethyl Acetate → HCID 53970540, compound

HRID 1608564Notes

Reaction equation

HRID 1608564 reaction equation
[OH:1][CH:2]1[C:13]2[C:14](=[O:15])[C:9]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:19])[CH3:18])([CH2:10][CH2:11][CH:12]=2)[C:8]#[C:7][CH:6]=[CH:5][C:4]#[C:3]1.FC(F)(F)S(O)(=O)=O.[C:32]([O:35][CH2:36]C)(=[O:34])[CH3:33]>CCOCC>[CH3:36][O:35][C:32]([CH2:33][C:12]1[CH:13]=[CH:14][C:9]([CH2:8][O:1][CH:2]2[C:13]3[C:14](=[O:15])[C:9]([O:16][Si:17]([C:20]([CH3:23])([CH3:22])[CH3:21])([CH3:18])[CH3:19])([CH2:10][CH2:11][CH:12]=3)[C:8]#[C:7][CH:6]=[CH:5][C:4]#[C:3]2)=[CH:10][CH:11]=1)=[O:34]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 62406Trifluoromethanesulfonic acidHCID 54135319HCID 54135319, compound

Product 1

HCID 53970540HCID 53970540, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

To a solution of the alcohol 6 (208 mg., 0.63 mmol) and imidate 7 (300 mg, 0.92 mmol) in 5 mL of anhydrous ether was added trifluoromethanesulfonic acid (25 μL, 0.28 mmol). The solution was diluted with ethyl acetate and washed with saturated bicarbonate. The organic fraction was dried over MgSO4, concentrated and the residue chromatographed over silica gel (5:1 hexane/ethyl acetate) to give compound 8a (184 mg, 59%) and 77 mg of recovered alcohol 1 (37%).

Workup

  1. washwashed with saturated bicarbonate
  2. dry with materialThe organic fraction was dried over MgSO4
  3. concentrationconcentrated
  4. customthe residue chromatographed over silica gel (5:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-30ef0f5285294083a08fa7d5a95c5262
Source dataset
uspto-grants-1995_03
Patent number
US05395849

Reaction notes

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