Trifluoromethanesulfonic acid → HCID 54487406, compound

HRID 1608563Notes

Reaction equation

HRID 1608563 reaction equation
[CH3:1][O:2][C:3]([CH2:5][C:6]1[CH:35]=[CH:34][C:9]([CH2:10][O:11][CH:12]2[C:23]3[C:24](=[O:25])[C:19]([O:26][Si](C(C)(C)C)(C)C)([CH2:20][CH2:21][CH:22]=3)[C:18]#[C:17][CH:16]=[CH:15][C:14]#[C:13]2)=[CH:8][CH:7]=1)=[O:4].FC(F)(F)S(O)(=O)=O>CCOCC.C(OCC)(=O)C>[OH:26][C:19]12[C:24](=[O:25])[C:23](=[CH:22][CH2:21][CH2:20]1)[CH:12]([O:11][CH2:10][C:9]1[CH:8]=[CH:7][C:6]([CH2:5][C:3]([O:2][CH3:1])=[O:4])=[CH:35][CH:34]=1)[C:13]#[C:14][CH:15]=[CH:16][C:17]#[C:18]2

Participants

5

Reactant 2

HCID 62406Trifluoromethanesulfonic acidHCID 53970540HCID 53970540, compound

Product 1

HCID 54487406HCID 54487406, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8857Ethyl AcetateSolvent

Procedure

The silyl ether (8a) was dissolved in 4 mL of anhydrous ether and treated with 100 mL of trifluoromethanesulfonic acid, diluted with ethyl acetate and washed with saturated bicarbonate. The organic fraction was dried over MgSO4 and the residue combined with compound 8b obtained above and chromatographed over silica gel (2:1 hexane/ethyl acetate) to give 50 mg (60%) of compound 8b as a colorless oil:

Workup

  1. washwashed with saturated bicarbonate
  2. dry with materialThe organic fraction was dried over MgSO4
  3. customobtained above and
  4. customchromatographed over silica gel (2:1 hexane/ethyl acetate)

Sources & evidence

ORD record
ord-ac35f906e1354562a703b93ea6d22723
Source dataset
uspto-grants-1995_03
Patent number
US05395849

Reaction notes

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