Cesium carbonate → HCID 24752878, compound

HRID 1675242Notes

Reaction equation

HRID 1675242 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[OH:7][C:8]1[CH:13]=[CH:12][C:11]([CH:14]([C:21]2[CH:25]=[CH:24][O:23][N:22]=2)[CH2:15][C:16]([O:18]CC)=[O:17])=[CH:10][CH:9]=1.[Cl:26][C:27]1[C:28]([CH3:41])=[C:29]([C:33]2[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=2)[CH2:36]Cl)[CH:30]=[CH:31][CH:32]=1.[I-].[Cs+]>CS(C)=O.[Cl-].[Na+].O.CCOC(C)=O>[Cl:26][C:27]1[C:28]([CH3:41])=[C:29]([C:33]2[CH:34]=[C:35]([CH:38]=[CH:39][CH:40]=2)[CH2:36][O:7][C:8]2[CH:9]=[CH:10][C:11]([CH:14]([C:21]3[CH:25]=[CH:24][O:23][N:22]=3)[CH2:15][C:16]([OH:18])=[O:17])=[CH:12][CH:13]=2)[CH:30]=[CH:31][CH:32]=1

Participants

8

Reactant 4

HCID 10796Cesium carbonateHCID 24601Cesium iodideHCID 57835925HCID 57835925, compoundHCID 59300636HCID 59300636, compound

Product 1

HCID 24752878HCID 24752878, compoundYield 44.7%

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Conditions

Temperature
35 °C

Procedure

Cesium carbonate (80 mg, 0.24 mmol) was added to a mixture of 1.1 (50 mg, 0.2 mmol), the benzyl chloride 1.4 (60 mg, 0.24 mmol) and CsI (catalytic amount) in DMSO (1 mL). The mixture was stirred at room temperature for 2 hours and at 35° C. for 4 hours. After cooling, the mixture was treated with EtOAc (5 mL) and brine (5 mL). The organic layer was separated, washed twice with brine, dried, and concentrated. The crude product was treated with THF (2 mL), MeOH (2 mL), water (1 mL) and NaOH (0.11 mL, 10 N). The mixture was stirred at room temperature for 4 hours. The organic solvent was blown away by nitrogen, and the aqueous mixture was acidified by adding HCl (0.35 mL, 3 N). The aqueous was extracted with DCM. The organic layer was dried, concentrated, and purified by flash chromatography to give 1 (40 mg). MS ESI (pos.) m/e: 448 (M+H). 1H NMR (CDCl3) δ 8.29 (d, 1H), 7.40 (m, 4H), 7.25 (m, 2H), 7.18 (m, 4H), 6.95 (d, 2H), 6.08 (d, 1H), 5.10 (s, 2H), 4.57 (t, 1H), 3.28 (dd, 1H), 2.99 (dd, 1H), 2.26 (s, 3H).

Workup

  1. temperatureAfter cooling
  2. customThe organic layer was separated
  3. washwashed twice with brine
  4. customdried
  5. concentrationconcentrated
  6. additionThe crude product was treated with THF (2 mL), MeOH (2 mL), water (1 mL) and NaOH (0.11 mL, 10 N)
  7. stirringThe mixture was stirred at room temperature for 4 hours
  8. additionby adding HCl (0.35 mL, 3 N)
  9. extractionThe aqueous was extracted with DCM
  10. customThe organic layer was dried
  11. concentrationconcentrated
  12. custompurified by flash chromatography

Sources & evidence

ORD record
ord-c4ac584f18814e8fbfb91e8be6f6e133
Source dataset
uspto-grants-2011_08
Patent number
US08003648B2

Reaction notes

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