Potassium Fluoride → P-[Tetrahydropyran-2-yloxy]phenylacetylene

HRID 1359183Notes

Reaction equation

HRID 1359183 reaction equation
[F-].[K+].[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]#[C:17][Si](C)(C)C)=[CH:12][CH:11]=1>CO>[O:3]1[CH2:8][CH2:7][CH2:6][CH2:5][CH:4]1[O:9][C:10]1[CH:11]=[CH:12][C:13]([C:16]#[CH:17])=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 522689Potassium FluorideHCID 10540306Silane, trimethyl[[4-[(tetrahydro-2H-pyran-2-yl)oxy]phenyl]ethynyl]-

Product 1

HCID 11310191P-[Tetrahydropyran-2-yloxy]phenylacetylene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

KF (9.3 g, 160 mmol) was added to a stirred solution of 2 (22.6 g, 80 mmol) in MeOH (150 ml). The reaction mixture was stirred at room temperature for about 4 hours. After the reaction finshed (GC shows no starting material remaining), the solvent was removed under reduced pressure on a rotary evaporator. The residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1) to give a pale yellow crystals of 3. Yield 15.7 g(97%); mp 65° C., δH(CDCl3; 300 MHz): 7.42(d, J=8.7, 2H, Ar—H), 7.00(d, J=8.7, 2H, Ar—H), 5.43(t, J=3.2, 1H, OCHO), 3.87(m, 1H, THP, 3.60(m, 1H, THP), 2.99(s, 1H, C═C—H), 1.96˜1.56(m, 6H, THP).

Workup

  1. customwas removed under reduced pressure on a rotary evaporator
  2. customThe residue was purified by column chromatography on silica gel (petroleum ether-ethyl acetate=9:1)
  3. customto give a pale yellow crystals of 3

Sources & evidence

ORD record
ord-bb1b2d5080344d65950a48c5889fad1f
Source dataset
uspto-grants-2003_07
Patent number
US06599945B2

Reaction notes

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