Cesium carbonate → HCID 21957496, compound

HRID 2213572Notes

Reaction equation

HRID 2213572 reaction equation
Br[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[CH3:3].[OH:10][C:11]1[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=1[O:19][CH2:20][CH2:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH:14]=[O:15].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C)C=O.C(OCC)(=O)C>[C:4]1([CH:2]([O:10][C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][C:18]=2[O:19][CH2:20][CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[CH:14]=[O:15])[CH3:3])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 11454(1-Bromoethyl)benzeneHCID 219574673-Hydroxy-4-(2-phenylethoxy)benzaldehyde

Product 1

HCID 21957496HCID 21957496, compoundYield 95.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

(1-Bromoethyl)benzene (0.56 mL, 4.13 mmol, 2 eq) was added to a stirred solution of 3-hydroxy-4-(2-phenylethoxy)-benzaldehyde (500 mg, 2.06 mmol, 1 eq) and cesium carbonate (672 mg, 2.06 mmol, 1 eq) in N,N-dimethylformamide (8 mL). The solution was stirred overnight and then diluted with ethyl acetate (50 mL). The organic solution was washed with 1M HCl (2×100 mL), and brine (100 mL), dried over sodium sulfate and evaporated. The residue was purified by chromatography on silica gel and elution with petroleum ether:ethyl acetate (6:1) gave the product as a colourless oil (680 mg, 95%). RF (petroleum ether:ethyl actetate, 4:1) 0.51. 1H NMR (CDCl3) δ 9.72 (s, 1H, O═C—H), 6.93 (d, 1H, J 7.9 Hz, ArH), 5.38 (q, 1H, J 6.4 Hz, CHCH3Ph), 4.33 (m, 2H, CH2CH2Ph), 3.21 (t, 2H, J 6.8 Hz, CH2CH2Ph), 1.67 (d, 3H, J 6.4 Hz, CHCH3Ph).

Workup

  1. washThe organic solution was washed with 1M HCl (2×100 mL), and brine (100 mL)
  2. dry with materialdried over sodium sulfate
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel and elution with petroleum ether:ethyl acetate (6:1)

Sources & evidence

ORD record
ord-1e0cb2677aa2467c9ca43452f1b7d302
Source dataset
uspto-grants-2006_09
Patent number
US07105554B2

Reaction notes

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