Sodium hydride → Methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoate

HRID 658005Notes

Reaction equation

HRID 658005 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([OH:15])[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:3])[CH3:2].Br[CH2:17][CH2:18][CH2:19][O:20][CH:21]1[CH2:26][CH2:25][CH2:24][CH2:23][O:22]1.[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[C:1]([C:5]1[CH:6]=[C:7]([CH:12]=[C:13]([O:15][CH2:17][CH2:18][CH2:19][O:20][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][O:22]2)[CH:14]=1)[C:8]([O:10][CH3:11])=[O:9])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 27779882-(3-Bromopropoxy)tetrahydro-2H-pyranHCID 53399216Methyl 3-tert-butyl-5-hydroxybenzoate

Product 1

HCID 58136886Methyl 3-tert-butyl-5-[3-(tetrahydropyran-2-yloxy)propoxy]benzoateYield 99.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Methyl 3-tert-butyl-5-hydroxybenzoate (O6.043; 3.22 g) and 2-(3-bromopropoxy)-tetrahydropyran (4.14 g) were dissolved in DMF (30 ml), and sodium hydride (445 mg) was added. After stirring at RT for 3 h, the mixture was left to stand overnight. Then the DMF was drawn off and the residue was taken up in EA, washed with water, dried, filtered and concentrated. 5.37 g of product were obtained.

Workup

  1. waitthe mixture was left
  2. waitto stand overnight
  3. washwashed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-6c663924441746d78936ab9aabd90f10
Source dataset
uspto-grants-2011_12
Patent number
US08076336B2

Reaction notes

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