Sodium hydride → HCID 69135032, compound

HRID 2222414Notes

Reaction equation

HRID 2222414 reaction equation
[O:1]1[CH2:6][CH2:5][CH:4]([OH:7])[CH2:3][CH2:2]1.[H-].[Na+].[C:10]([O:14][CH2:15][CH2:16]Br)([CH3:13])([CH3:12])[CH3:11].[Cl-].[NH4+]>CN(C=O)C.C1OCCOCCOCCOCCOC1.[I-].[Na+]>[C:10]([O:14][CH2:15][CH2:16][O:7][CH:4]1[CH2:5][CH2:6][O:1][CH2:2][CH2:3]1)([CH3:13])([CH3:12])[CH3:11]

Participants

8

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 74956Tetrahydro-4H-pyran-4-olHCID 123592832-(2-Bromoethoxy)-2-methylpropane

Product 1

HCID 69135032HCID 69135032, compoundYield 64%

Reagents, catalysts & solvents 3

HCID 5238Sodium IodideCatalystHCID 3633615-Crown-5CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

Tetrahydropyran-4-ol (19.72 g; 0.193 mol) was added dropwise (rapid addition) to a suspension of sodium hydride (8.5 g; 0.213 mol) in DMF (200 ml) under argon. The mixture was heated at 50° C. for 40 minutes then cooled to ambient temperature. 2-tert-Butoxyethyl bromide (35 g, 0.193 mol), (J. Med. Chem. 1966, 361), was added dropwise followed by sodium iodide (approximately 1 g) and 15-crown-5 (20 drops). The mixture was heated at 105° C. for 1 hour. Upon cooling to ambient temperature the mixture was poured into a saturated solution of ammonium chloride and extracted with ether (2×1 l). The organic phase was washed with water, brine, dried (MgSO4) and the solvent evaporated off to give 4-(2-tert-butoxyethoxy)tetrahydropyran (25 g, 64%) as a light brown oil.

Workup

  1. addition(rapid addition)
  2. temperaturethen cooled to ambient temperature
  3. temperatureThe mixture was heated at 105° C. for 1 hour
  4. temperatureUpon cooling to ambient temperature the mixture
  5. extractionextracted with ether (2×1 l)
  6. washThe organic phase was washed with water, brine
  7. dry with materialdried (MgSO4)
  8. customthe solvent evaporated off

Sources & evidence

ORD record
ord-52b90deeadaf49dd93888b19656a68a9
Source dataset
uspto-grants-2008_05
Patent number
US07371765B2

Reaction notes

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