Diethyl Ether → HCID 20770788, compound

HRID 1814164Notes

Reaction equation

HRID 1814164 reaction equation
[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:13]=[CH:12][C:11]([SH:14])=[CH:10][CH:9]=2)[CH2:7][CH2:6]1)=[O:4].Cl[CH2:16][C:17]1[CH:22]=[CH:21][C:20]([C:23]2[CH:28]=[CH:27][C:26]([C:29]([F:32])([F:31])[F:30])=[CH:25][CH:24]=2)=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].CCOCC>C(#N)C.O>[F:30][C:29]([F:31])([F:32])[C:26]1[CH:25]=[CH:24][C:23]([C:20]2[CH:21]=[CH:22][C:17]([CH2:16][S:14][C:11]3[CH:12]=[CH:13][C:8]([C:5]4([C:3]([OH:2])=[O:4])[CH2:7][CH2:6]4)=[CH:9][CH:10]=3)=[CH:18][CH:19]=2)=[CH:28][CH:27]=1.[CH3:1][O:2][C:3]([C:5]1([C:8]2[CH:9]=[CH:10][C:11]([S:14][CH2:16][C:17]3[CH:18]=[CH:19][C:20]([C:23]4[CH:28]=[CH:27][C:26]([C:29]([F:30])([F:31])[F:32])=[CH:25][CH:24]=4)=[CH:21][CH:22]=3)=[CH:12][CH:13]=2)[CH2:6][CH2:7]1)=[O:4]

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 10796Cesium carbonateHCID 114599214-(4-Trifluoromethylphenyl)benzylchlorideHCID 11984183HCID 11984183, compound

Product 2

HCID 11984464HCID 11984464, compoundHCID 20770788HCID 20770788, compoundYield 134,917.297%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

Compound 36C (416 mg, 2.0 mmol) was dissolved in acetonitrile (50 mL) with example 36E (568 mg, 2.1 mmol) and Cs2CO3 (1.3 g, 4.0 mmol). The reaction mixture was stirred at RT overnight. Ether (50 mL) and H2O were added and stirring was continued for another 5 min. The layers were separated and the aqueous layer was extracted with ether (2×100 mL). The combined organics was dried over MgSO4 and concentrated to an oil. The crude product was purified by column chromatography eluted with EtOAc and hexanes to give the desired product, compound 36F as a thick yellow oil (597 g, 68%). MS: 443 (M+1)+.

Workup

  1. stirringstirring
  2. waitwas continued for another 5 min
  3. customThe layers were separated
  4. extractionthe aqueous layer was extracted with ether (2×100 mL)
  5. dry with materialThe combined organics was dried over MgSO4
  6. concentrationconcentrated to an oil
  7. customThe crude product was purified by column chromatography
  8. washeluted with EtOAc and hexanes

Sources & evidence

ORD record
ord-1f7ebda563214eacacef74498ab41f8f
Source dataset
uspto-grants-2005_04
Patent number
US06875780B2

Reaction notes

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