Benzaldehyde → 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol

HRID 1403466Notes

Reaction equation

HRID 1403466 reaction equation
[CH2:1]([O:4][CH:5]1[CH2:10][CH2:9][CH2:8][CH2:7][O:6]1)[C:2]#[CH:3].[Li]CCCC.[CH:16](=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C([O-])(O)=O.[Na+]>C1COCC1>[C:17]1([CH:16]([OH:23])[C:3]#[C:2][CH2:1][O:4][CH:5]2[CH2:10][CH2:9][CH2:8][CH2:7][O:6]2)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 98609Tetrahydro-2-(2-propynyloxy)-2H-pyranHCID 516892Sodium BicarbonateHCID 178418339Butyllithium

Product 1

HCID 706652771-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

To a solution of 2-(prop-2-ynyloxy)-tetrahydro-2H-pyran (10.0 g, 71.4 mmol) in THF (40 mL) was added n-BuLi (2.5M, 31.4 mL, 78.6 mmol) at −78° C. The reaction mixture was kept for 1 h at −78° C. and then benzaldehyde (8.3 g, 78.6 mmol) was added at −78° C. The reaction mixture was stirred for 2 h and then slowly warmed to −30° C. before being poured into NaHCO3 (aq., 500 mL), extracted with ethyl acetate (3×200 mL), dried over anhydrous sodium sulfate and then concentrated in vacuo to afford 1-phenyl-4-(tetrahydro-2H-pyran-2-yloxy)but-2-yn-1-ol as a colorless oil (17.0 g, crude).

Workup

  1. extractionextracted with ethyl acetate (3×200 mL)
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8404a5a4071745c2a48ceb630f6f0e9b
Source dataset
uspto-grants-2014_12
Patent number
US08912188B2

Reaction notes

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