Tetrahydrofuran → 3-(2H-pyran-4(3H,5H,6H)-ylidene)propan-1-ol

HRID 253576Notes

Reaction equation

HRID 253576 reaction equation
[PH4+].[Li]CCCC.[O:7]1[CH2:12][CH2:11][C:10](=O)[CH2:9][CH2:8]1.[CH2:14]1C[O:17][CH2:16][CH2:15]1>>[O:7]1[CH2:12][CH2:11][C:10](=[CH:14][CH2:15][CH2:16][OH:17])[CH2:9][CH2:8]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 121599Tetrahydro-4H-pyran-4-oneHCID 5460504PhosphoniumHCID 178418339Butyllithium

Product 1

HCID 574196163-(2H-pyran-4(3H,5H,6H)-ylidene)propan-1-olYield 61%

Procedure

To a suspension of the phosphonium salt (90.2 g, 1.5 eq) in dry THF (1100 mL) at 0° C. under nitrogen atmosphere was added n-BuLi (2.5 M, 216 mL, 0.54 mol). The solution was stirred for 1 h, followed by addition of dihydro-2H-pyran-4(3H)-one (15 g, 0.15 mol). Stirring was continued at rt overnight. The mixture was quenched with satd aq NH4Cl, and then filtered. The filtrate was dried over Na2SO4, and concentrated under vacuum to give the crude product, which was purified by column chromatography to give the product (13.1 g, 61%). 1H NMR (CD3OD) δ 2.1-2.3 (m, 6H), 2.5 (s, 1H), 3.5-3.7 (m, 6H), 5.1-5.2 (t, 1H).

Workup

  1. stirringStirring
  2. waitwas continued at rt overnight
  3. customThe mixture was quenched with satd aq NH4Cl
  4. filtrationfiltered
  5. dry with materialThe filtrate was dried over Na2SO4
  6. concentrationconcentrated under vacuum
  7. customto give the crude product, which
  8. customwas purified by column chromatography

Sources & evidence

ORD record
ord-8fa428f4e2184faeb7decfb537d2531f
Source dataset
uspto-grants-2011_01
Patent number
US07872028B2

Reaction notes

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