Water → HCID 66809070, compound

HRID 1913853Notes

Reaction equation

HRID 1913853 reaction equation
[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[CH:5][CH:4]=1.[CH2:16]([Li])CCC.CI.O>C1COCC1>[CH3:1][O:2][C:3]1[CH:15]=[CH:14][C:6]([O:7][CH:8]2[CH2:13][CH2:12][CH2:11][CH2:10][O:9]2)=[C:5]([CH3:16])[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 108998152-(4-Methoxyphenoxy)oxaneHCID 178418339Butyllithium

Product 1

HCID 66809070HCID 66809070, compoundYield 99.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

Dissolve 2-(4-methoxyphenoxy)tetrahydro-2H-pyran (20 g, 96 mmol, Preparation 27) in 200 mL anhydrous THF at 0° C. under nitrogen atmosphere. Add n-butyl lithium (n-BuLi) (78 mL, 1.6 M in hexanes, 125 mmol) dropwise via an additional funnel. Stir the resulting mixture at 0° C. for 3 hours. Add CH3I (7.8 mL, 125 mmol) in one batch. After 10 minutes add water. Rotary evaporate off volatiles, extract residue with Et2O and dry to give 21.3 g (100%) of 2-(4-methoxy-2-methyl-phenoxy)tetrahydro-2H-pyran as a yellow oil (21.3 g, 100%). 1H NMR (400 MHz, CDCl3) δ 7.03 (d, J=8.8 Hz, 1H), 6.75 (d, J=3.0 Hz, 1H), 6.68 (dd, J=8.8, 3.1 Hz, 1H), 5.30 (t, J=3.3 Hz, 1H), 3.96 (ddd, J=12.0, 9.2, 3.1 Hz, 1H), 3.78 (s, 3H), 3.67-3.56 (m, 1H), 2.28 (s, 3H), 2.10-1.96 (m, 1H), 1.94-1.83 (m, 2H), 1.67 (m, 3H). 13C NMR (101 MHz, CDCl3) δ 154.14, 149.33, 128.78, 116.55, 115.79, 111.08, 97.20, 62.15, 55.56, 30.73, 25.38, 19.14, 16.55.

Workup

  1. customRotary evaporate off volatiles
  2. extractionextract residue with Et2O
  3. customdry

Sources & evidence

ORD record
ord-97dc3bc156a54a4fbdcab2d8d6b4a1e0
Source dataset
uspto-grants-2013_12
Patent number
US08609794B2

Reaction notes

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