Tetrahydrofuran → 3-(dihydro-2H-pyran-3(4H)-ylidene)propan-1-ol

HRID 452005Notes

Reaction equation

HRID 452005 reaction equation
[PH4+].[Li]CCCC.[O:7]1[CH2:12][CH2:11][CH2:10][C:9](=O)[CH2:8]1.[CH2:14]1C[O:17][CH2:16][CH2:15]1>>[O:7]1[CH2:12][CH2:11][CH2:10][C:9](=[CH:14][CH2:15][CH2:16][OH:17])[CH2:8]1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 901092H-Pyran-3(4H)-one, dihydro-HCID 5460504PhosphoniumHCID 178418339Butyllithium

Product 1

HCID 673669913-(dihydro-2H-pyran-3(4H)-ylidene)propan-1-olYield 69%

Procedure

To a suspension of the phosphonium salt (69 g, 1.5 eg) in dry THF (1100 mL) at 0° C. under nitrogen atmosphere was added n-BuLi (2.5 M, 111 mL, 0.413 mol). The solution was stirred for 1 hr, followed by addition of dihydro-2H-pyran-3(4H)-one (11.5 g, 0.115 mol). Stirring was continued at rt overnight. The mixture was quenched by sat. aq. NH4Cl, and then filtered. The filtrate was dried over Na2SO4, and concentrated in vacuo to give the crude product, which was purified through column chromatography to give 3-(dihydro-2H-pyran-3(4H)-ylidene)propan-1-ol (11.2 g, 69%). 1H NMR (CD3OD): δ 4.2-3.9 (d, 2H), 3.8-3.5 (m, 4H), 2.4-2.2 (m, 4H), 5.3-5.2 (d, 1H), 2.1-1.8 (s, 1H), 1.8-1.6 (m, 2H).

Workup

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

Sources & evidence

ORD record
ord-f8d86527fb4044639cc9b08a2b1e959c
Source dataset
uspto-grants-2013_07
Patent number
US08487108B2

Reaction notes

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