Cyclopentanone → HCID 23496719, compound

HRID 1836940Notes

Reaction equation

HRID 1836940 reaction equation
[Mg].Cl[CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[C:8]1(=[O:13])[CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl-].[NH4+]>C1COCC1>[CH3:5][Si:4]([CH2:3][C:8]1([OH:13])[CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 8452CyclopentanoneHCID 25517Ammonium ChlorideHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224Magnesium

Product 1

HCID 23496719HCID 23496719, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A flask was charged with 14.6 g of magnesium and 120 ml of THF, to which a solution of 67.5 g of chloromethyltrimethylsilane diluted with 70 ml of THF was added dropwise at 50° C. The addition was followed by one hour of stirring at 65° C., after which 42.1 g of cyclopentanone was added dropwise below 20° C. After one hour of stirring at room temperature, an aqueous solution of ammonium chloride was added for hydrolysis. This was followed by ordinary post-treatments. Upon vacuum distillation, there was obtained 70.6 g (yield 82%) of 1-trimethylsilylmethylcyclopentanol.

Workup

  1. additionwas added dropwise at 50° C
  2. additionThe addition
  3. stirringAfter one hour of stirring at room temperature
  4. distillationUpon vacuum distillation

Sources & evidence

ORD record
ord-7214b5edc8eb46729b182f1cd613fcc9
Source dataset
uspto-grants-2004_08
Patent number
US06780563B2

Reaction notes

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