Chlorotrimethylsilane → HCID 12163517, compound

HRID 1106893Notes

Reaction equation

HRID 1106893 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@H:15]([OH:18])[CH2:16]O)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC(C)(C)C([O-])([O-])[O-].Cl[Si](C)(C)C.C(=O)([O-])[O-].[K+].[K+].[Cl-].[NH4+]>ClCCl.CO>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([C@H:15]2[CH2:16][O:18]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

8

Reactant 5

HCID 6397ChlorotrimethylsilaneHCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 21927715TrimethylorthoacetateHCID 54078618HCID 54078618, compound

Product 1

HCID 12163517HCID 12163517, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of Example 2 (16.22 g, 66 mmol) in dichloromethane (150 mL), trimethylorthoacetate (10.0 mL, 79 mmol) and chlorotrimethylsilane (10.0 mL, 79 mmol) were added. The reaction was stirred at room temperature under argon for 2 hours, then the solvent removed in vacuo. Potassium carbonate (11.59 g, 84 mmol) and methanol (260 mL) were added, and the reaction was stirred at room temperature under argon for 2 hours then poured into saturated ammonium chloride solution (550 mL) and extracted with dichloromethane (1650 mL). The organics were dried (MgSO4) and the solvent removed in vacuo. Column chromatography (heptane:ethyl acetate 4:1) gave the product as a yellow oil, 56 mmol, 85%.

Workup

  1. customthe solvent removed in vacuo
  2. stirringthe reaction was stirred at room temperature under argon for 2 hours
  3. extractionextracted with dichloromethane (1650 mL)
  4. dry with materialThe organics were dried (MgSO4)
  5. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-b6db0748fc5f4fecb42f682194a78d05
Source dataset
uspto-grants-2000_05
Patent number
US06057357

Reaction notes

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