Ethyl Bromide → 1-(3-Cyclohexylmethoxy-5-ethoxyphenyl)ethanone

HRID 217726

Reaction equation

HRID 217726 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([OH:8])[CH:7]=1.[CH2:12](Br)[CH3:13].[H-].[Na+].[CH:17]1([CH2:23]Br)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1>CN(C=O)C.CC(=O)OCC>[CH:17]1([CH2:23][O:1][C:2]2[CH:3]=[C:4]([C:9](=[O:11])[CH3:10])[CH:5]=[C:6]([O:8][CH2:12][CH3:13])[CH:7]=2)[CH2:22][CH2:21][CH2:20][CH2:19][CH2:18]1

Participants

7

Reactant 4

HCID 6332Ethyl BromideHCID 24758Sodium hydride2×HCID 1039933',5'-DihydroxyacetophenoneHCID 137636Cyclohexane, (bromomethyl)-

Product 1

HCID 581368361-(3-Cyclohexylmethoxy-5-ethoxyphenyl)ethanone

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

1-(3,5-Dihydroxyphenyl)ethanone (1.0 g) and ethyl bromide (0.531 ml) were dissolved at RT in DMF (20 ml), and sodium hydride (189 mg) was added. After stirring at 50° C. for 2 h, cyclohexylmethyl bromide (1.36 ml) was added, followed by further sodium hydride (315 mg). After stirring at 50° C. for another 2 h, the DMF was drawn off and the residue was taken up in EA, washed with water, dried, filtered and concentrated. The residue was purified using silica gel (80 g cartridge, n-heptane/EA gradient of 0-20% within 60 min). 378 mg of the title compound were obtained. LC-MS rt: 2.07 min [M+H]+: 277.2 (met. a)

Workup

  1. stirringAfter stirring at 50° C. for another 2 h
  2. washwashed with water
  3. customdried
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified
  7. customsilica gel (80 g cartridge, n-heptane/EA gradient of 0-20% within 60 min)

Sources & evidence

ORD record
ord-441edbb569074703bb411e949a19166b
Source dataset
uspto-grants-2012_06
Patent number
US08198272B2

Linked notes

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