Cyclopentanecarbonyl chloride → HCID 55298626, compound

HRID 1453331Notes

Reaction equation

HRID 1453331 reaction equation
[CH:1]1([C:6](Cl)=[O:7])[CH2:5][CH2:4][CH2:3][CH2:2]1.[Al+3].[Cl-:10].[Cl-].[Cl-].[CH:13]([Si](C)(C)C)=[CH2:14]>C(Cl)Cl>[Cl:10][CH2:13][CH2:14][C:6]([CH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7]

Participants

5

Reactant 3

HCID 78284Cyclopentanecarbonyl chlorideHCID 79102VinyltrimethylsilaneHCID 6451240Aluminum(III) Chloride

Product 1

HCID 55298626HCID 55298626, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of cyclopentanecarbonyl chloride (10 g, 75 mmol) and AlCl3 (11.1 g, 83 mmol) in CH2Cl2 (100 mL) was cooled to −10° C. A solution of vinyltrimethylsilane (12 mL, 75 mmol) in CH2Cl2 (50 mL) was added drop wise over 30 minutes. The reaction was stirred for 20 additional minutes, and then poured over 200 g of ice. The layers were separated, and the aqueous layer was extracted with CH2Cl2. The organic layers were combined and washed with saturated NaHCO3. The organic was then dried over Na2SO4, the solids were filtered away, and the product was purified by distillation (7.17 g, 60%). 1H NMR (CDCl3) δ: 1.43-1.70 (m, 8H), 2.69-2.80 (m, 3H), 3.61 (t, J=6.57 Hz, 2H).

Workup

  1. customThe layers were separated
  2. extractionthe aqueous layer was extracted with CH2Cl2
  3. washwashed with saturated NaHCO3
  4. dry with materialThe organic was then dried over Na2SO4
  5. filtrationthe solids were filtered away
  6. distillationthe product was purified by distillation (7.17 g, 60%)

Sources & evidence

ORD record
ord-07a2d1b9f3c943a49f7e9ef67d40a134
Source dataset
uspto-grants-2009_01
Patent number
US07473790B2

Reaction notes

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