Cesium carbonate → HCID 86700872, compound

HRID 881767Notes

Reaction equation

HRID 881767 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([OH:19])[CH2:13][CH2:12][C:11](=[CH:14][C:15]([O:17][CH3:18])=[O:16])[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]23[O:19][C:11]([CH2:14][C:15]([O:17][CH3:18])=[O:16])([CH2:10][CH2:9]2)[CH2:12][CH2:13]3)=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 10796Cesium carbonateHCID 86700873Acetic acid, 2-[4-(4-bromophenyl)-4-hydroxycyclohexylidene]-, methyl ester

Product 1

HCID 86700872HCID 86700872, compoundYield 34%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 2-(4-(4-bromophenyl)-4-hydroxycyclohexylidene)acetate (190 mg, 0.58 mmol) in acetonitrile (7 mL) was added Cs2CO3 (381 mg, 1.17 mmol) and the reaction was let stir in a 50° C. oil bath for 24 h. The resulting reaction mixture was diluted with ethyl acetate and washed with water, followed by a saturated aqueous NaCl solution. The organic phase was dried over MgSO4, filtered and concentrated by rotary evaporation in vacuo to afford 188 mg of crude orange film. The crude material was purified by column chromatography (24 g silica gel, 0-40% EtOAc:Hept, monitor 230 nm) to afford 64 mg (34%) of the title compound as a colorless film that solidified upon standing. 1H NMR (400 MHz, DMSO-d6): δ ppm 1.56-1.81 (m, 4H), 1.85-1.97 (m, 2H), 2.14 (td, J=9.9, 3.9 Hz, 2H), 2.92 (s, 2H), 3.63 (s, 3H), 7.32 (d, J=8.6 Hz, 2H), 7.53 (d, J=8.6 Hz, 2H). 13C NMR (100 MHz, DMSO-d6): δ ppm 170.3, 142.0, 130.9, 127.1, 119.8, 86.0, 83.2, 51.3, 37.6, 35.4 (additional signal likely hidden under DMSO solvent signal). ESI-MS m/z: 327.0 [M+H]+, retention time 1.55 min (condition E).

Workup

  1. customThe resulting reaction mixture
  2. washwashed with water
  3. dry with materialThe organic phase was dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated by rotary evaporation in vacuo
  6. customto afford 188 mg of crude orange film
  7. customThe crude material was purified by column chromatography (24 g silica gel, 0-40% EtOAc:Hept, monitor 230 nm)

Sources & evidence

ORD record
ord-8ed9d48e23ec4abd84c4d5857d8be2a1
Source dataset
uspto-grants-2015_03
Patent number
US08993619B2

Reaction notes

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