Acetic Acid → HCID 57983635, compound

HRID 1869064Notes

Reaction equation

HRID 1869064 reaction equation
C[Si]([C:5]#[C:6][C:7]1[CH:8]=[CH:9][C:10](=[O:13])[O:11][CH:12]=1)(C)C.C(O)(=O)C.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:6]([C:7]1[CH:8]=[CH:9][C:10](=[O:13])[O:11][CH:12]=1)#[CH:5]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 2724141Tetrabutylammonium FluorideHCID 68948802HCID 68948802, compound

Product 1

HCID 57983635HCID 57983635, compoundYield 96.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 5-[(trimethylsilyl)ethynyl]-2H-pyran-2-one (0.5 g, 2.6 mmol) and acetic acid (0.6 g, 10 mmol) in THF (50 mL) at 0° C. was added dropwise over 10 min tetrabutylammonium fluoride. The mixture was stirred for 1 h at 0° C. then was partitioned between sat. NaHCO3 and ether. The organic phase was washed with brine then dried (MgSO4). The solvent was passed through a plug of silica gel and then evaporated to give the title compound (0.30 g, 96%) as an off white solid; mp 99-100° C. 1H NMR (CDCl3 , 300 MHz): δ 7.73 (dd, 1H), 7.33 (dd, 1H), 6.32 (dd, 1H), 3.11 (s, 1H). 13C NMR (CDCl3 , 300 MHz) 159.4; 155.7; 144.6; 116.1; 103.3; 80.7; 75.7. Anal. Calc'd for C7H4O2: C, 70.00; H 3.36. Found: C, 70.09; H, 3.47.

Workup

  1. customthen was partitioned between sat. NaHCO3 and ether
  2. washThe organic phase was washed with brine
  3. dry with materialthen dried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-57ca0dcbb7984387aa9dd9fd66777539
Source dataset
uspto-grants-2009_12
Patent number
US07635741B2

Reaction notes

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