Cycloheptanone → HCID 68797590, compound

HRID 2059761Notes

Reaction equation

HRID 2059761 reaction equation
[C:1]1(=[O:8])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.Br[CH2:10][C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=1[CH2:17]Br.CC(C)([O-])C.[K+]>C1(C)C=CC=CC=1>[CH2:17]1[C:12]2[C:11](=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH2:10][C:2]21[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:1]2=[O:8]

Participants

5

Reactant 3

HCID 10400CycloheptanoneHCID 66665o-Bis(bromomethyl)benzeneHCID 23665647Potassium tert-butoxide

Product 1

HCID 68797590HCID 68797590, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
85 °C

Procedure

A solution of cycloheptanone (5.30 mL, 45.0 mmol) and 1,2-bis(bromomethyl)benzene (11.88 g, 45.0 mmol) in toluene (65 mL) was treated all at once with potassium tert-butoxide (10.10 g, 90 mmol). The reaction stirred for 20 hours at 85° C. After this time, the mixture was washed with 25 mL water and 65 mL of 15% HCl, then the aqueous washes were extracted three times with ether. The combined organics were washed with brine, dried over Na2SO4, and evaporated to a yellow oil, which was purified by chromatography on silica gel (93:7 to 85:15 EtOAc-hexane, eluant) to afford the title compound. 1H NMR (300 MHz, d6-DMSO) δ 7.09-7.18 (m, 4H), 3.26 (d, J=16.0 Hz, 2H), 2.75 (d, J=16.0, 2H), 2.59 (m, 2H), 1.84 (m, 2H), 1.57-1.66 (m, 4H), 1.47 (m, 2H). MS (DCI+) m/z 215 (M+H, 232 (M+NH4).

Workup

  1. washAfter this time, the mixture was washed with 25 mL water and 65 mL of 15% HCl
  2. extractionthe aqueous washes were extracted three times with ether
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. customevaporated to a yellow oil, which
  6. customwas purified by chromatography on silica gel (93:7 to 85:15 EtOAc-hexane, eluant)

Sources & evidence

ORD record
ord-e5ea6ba626614f0094bb60abab08d8a1
Source dataset
uspto-grants-2012_10
Patent number
US08278313B2

Reaction notes

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