Chlorotrimethylsilane → HCID 67023905, compound

HRID 1673209Notes

Reaction equation

HRID 1673209 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].BrCCBr.Cl[Si](C)(C)C.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]2[CH:25]=[C:26]3[C:41](=[O:42])[CH2:40][C:39]([CH3:44])([CH3:43])[O:38][C:27]3=[N:28][C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])=[CH:20][CH:19]=1>C1COCC1.CCOC(C)=O.[Zn]>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([C:24]2[CH:25]=[C:26]3[C:41]([CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4])([OH:42])[CH2:40][C:39]([CH3:44])([CH3:43])[O:38][C:27]3=[N:28][C:29]=2[C:30]2[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][C:31]=2[Cl:37])=[CH:22][CH:23]=1

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 7748Ethyl bromoacetateHCID 78391,2-DibromoethaneHCID 24996234HCID 24996234, compound

Product 1

HCID 67023905HCID 67023905, compound

Reagents, catalysts & solvents 3

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent2×HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
65 °C

Procedure

A mixture of ethyl 2-bromoacetate (0.334 mL 3.01 mmol), 1,2-dibromoethane (0.02 mL, 0.23 mmol), Zn powder (0.227 g, 3.47 mmol) and THF (2.5 mL) was heated to 65° C. for 2 min before cooling to rt. Chlorotrimethylsilane (0.015 mL, 0.116 mmol) was added and the reaction was stirred for 5 min at which point the product of Example 1 (1 g, 2.315 mmol) in THF 10 mL was added. The reaction was heated to 70° C. After 1 h the reaction was cooled to rt. The reaction was diluted with EtOAc and washed with 2 M aq HCl and brine. The concentrated residue was purified by flash chromatography on silica gel gradient eluted with 0-10% EtOAc in CH2Cl2 affording the product (LC-2) HPLC/MS: 520.2 (M+1), 522.2 (M+3); Rt=3.97 min.

Workup

  1. temperaturebefore cooling to rt
  2. additionwas added
  3. temperatureThe reaction was heated to 70° C
  4. temperatureAfter 1 h the reaction was cooled to rt
  5. washwashed with 2 M aq HCl and brine
  6. customThe concentrated residue was purified by flash chromatography on silica gel gradient
  7. washeluted with 0-10% EtOAc in CH2Cl2 affording the product (LC-2) HPLC/MS

Sources & evidence

ORD record
ord-8849b0597e73494ab60fba7ab752ddb7
Source dataset
uspto-grants-2011_08
Patent number
US07999107B2

Reaction notes

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