Tetrahydrofuran → HCID 58000830, compound

HRID 2358265Notes

Reaction equation

HRID 2358265 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]2=[C:6]3[N:17]=[C:16]([C:18]4[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:25])[NH:15][C:7]3=[C:8]3[C:13]([C:12](=[O:14])[NH:11][CH:10]=[CH:9]3)=[C:4]2[CH:3]=1.CC(C)([O-])C.[K+].[CH3:34][Si:35]([CH2:38][CH2:39][O:40][CH2:41]Cl)([CH3:37])[CH3:36].C1[CH2:47][O:46][CH2:45][CH2:44]1>>[Br:1][C:2]1[CH:27]=[CH:26][C:5]2=[C:6]3[N:17]=[C:16]([C:18]4[C:23]([F:24])=[CH:22][CH:21]=[CH:20][C:19]=4[Cl:25])[N:15]([CH2:47][O:46][CH2:45][CH2:44][Si:35]([CH3:37])([CH3:36])[CH3:34])[C:7]3=[C:8]3[C:13]([C:12](=[O:14])[N:11]([CH2:41][O:40][CH2:39][CH2:38][Si:35]([CH3:37])([CH3:36])[CH3:34])[CH:10]=[CH:9]3)=[C:4]2[CH:3]=1

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 27242712-Chloromethyl 2-(trimethylsilyl)ethyl etherHCID 23665647Potassium tert-butoxideHCID 178518678HCID 178518678, compound

Product 1

HCID 58000830HCID 58000830, compound

Procedure

The intermediate from Example 1 Step E (1.76 g, 3.99 mmol) was suspended in 150 mL THF and the flask was immersed in a room temperature water bath followed by the addition 11 mL (2.7 equiv) of a 1M solution of potassium tert-butoxide (in THF). After 45 minutes, 1.79 g of SEMCl (2.7 equiv) was added. The reaction was allowed to warm to ambient temperature overnight. The volatiles were removed in vacuo and the crude residue was dissolved in EtOAc and washed sequentially with a saturated solution of NaHCO3 and brine. The solution was dried with MgSO4 and filtered. Evaporation of the solvent under reduced pressure provided the crude residue that was purified on silica gel (gradient elution from 0 to 30% EtOAc/hexanes).

Workup

  1. customwas immersed in a room temperature
  2. customThe volatiles were removed in vacuo
  3. dissolutionthe crude residue was dissolved in EtOAc
  4. washwashed sequentially with a saturated solution of NaHCO3 and brine
  5. dry with materialThe solution was dried with MgSO4
  6. filtrationfiltered
  7. customEvaporation of the solvent under reduced pressure

Sources & evidence

ORD record
ord-cf059515366a4e6da70b5b21127b6f58
Source dataset
uspto-grants-2010_07
Patent number
US07763634B2

Reaction notes

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