Sodium hydride → HCID 58045966, compound

HRID 1524573Notes

Reaction equation

HRID 1524573 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([OH:13])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:3])[CH3:2].Br[CH2:18][CH2:19][O:20][CH3:21].[H-].[Na+]>CN(C=O)C.CC(=O)OCC>[C:1]([C:5]1[CH:6]=[C:7]([C:14](=[O:16])[CH3:15])[CH:8]=[C:9]([O:13][CH2:18][CH2:19][O:20][CH3:21])[C:10]=1[O:11][CH3:12])([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 809722-Bromoethyl methyl etherHCID 581369461-(3-Tert-butyl-5-hydroxy-4-methoxyphenyl)ethanone

Product 1

HCID 58045966HCID 58045966, compoundYield 46.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

1-(3-tert-Butyl-5-hydroxy-4-methoxyphenyl)ethanone (O3.070; 2.00 g) and 1-bromo-2-methoxyethane (1.5 g) were dissolved in DMF (20 ml), and sodium hydride (259 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. The EA phase was washed with water, dried, filtered and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/EA 0-40% within 60 min). 1.17 g of the title compound were obtained.

Workup

  1. waitthe mixture was left
  2. waitto stand overnight
  3. washThe EA phase was washed with water
  4. customdried
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified
  8. customsilica gel (80 g cartridge, n-heptane/EA 0-40% within 60 min)

Sources & evidence

ORD record
ord-e30ce91fa819446097f576a2edd81e68
Source dataset
uspto-grants-2015_07
Patent number
US09079906B2

Reaction notes

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