Sodium hydride → 4-Methoxy-4-[3-((napth-2-yl)methoxy)-prop-1-ynyl]tetrahydropyran

HRID 326230Notes

Reaction equation

HRID 326230 reaction equation
[CH3:1][O:2][C:3]1([C:9]#[C:10][CH2:11][OH:12])[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.[H-].[Na+].Br[CH2:16][C:17]1[CH:26]=[CH:25][C:24]2[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=2)[CH:18]=1>C1COCC1.CN(C=O)C>[CH3:1][O:2][C:3]1([C:9]#[C:10][CH2:11][O:12][CH2:16][C:17]2[CH:26]=[CH:25][C:24]3[C:19](=[CH:20][CH:21]=[CH:22][CH:23]=3)[CH:18]=2)[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 703202-BromomethylnaphthaleneHCID 193880394-Methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran

Product 1

HCID 99266964-Methoxy-4-[3-((napth-2-yl)methoxy)-prop-1-ynyl]tetrahydropyran

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

4-methoxy-4-(3-hydroxyprop-1-ynyl)tetrahydropyran (1.2 g, 6.97 mmol) was treated with sodium hydride in THF (18 mL). After gas evolution ceased, a solution of 2-(bromomethyl)napthalene (1.70 g, 7.67 mmol) in dry DMF (9 mL) was added. After 3 hours at ambient temperature the reaction was quenched with saturated aqueous ammonium chloride. The resulting two-phase mixture was extracted with ether (3×100 mL). The combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. Purification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes) provided the title compound. (2.00 g, 92%) as a colorless oil. 1H NMR (300 MHz, CDCl3); 7.80-7.90 (4H, m), 7.47-7.52 (3H, m), 4.70 (2H, s), 4.32 (2H, s), 3.87 (2H, dd, J=12,4.5 Hz), 3.67 (2H, dd, J=12,3 Hz), 3.40 (3H, s), 1.95 (2H, br d, J=13 Hz), 1.49 (2H, ddd, J=13,9,4.5 Hz); MS (M+NH4)+ =328. Analysis calc'd for C20H22O3 : C, 77.39; H, 7.14; Found: C, 76.10; H, 7.10.

Workup

  1. customAfter 3 hours at ambient temperature the reaction was quenched with saturated aqueous ammonium chloride
  2. extractionThe resulting two-phase mixture was extracted with ether (3×100 mL)
  3. dry with materialThe combined organic layers were dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by chromatography on silica gel (100 g, 10% ethyl acetate: hexanes)

Sources & evidence

ORD record
ord-d9ca71202cbd45f6b7de4daec16ade00
Source dataset
uspto-grants-1993_12
Patent number
US05268379

Reaction notes

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