Cyclohexanone → HCID 4128986, compound

HRID 1836939Notes

Reaction equation

HRID 1836939 reaction equation
[Mg].Cl[CH2:3][Si:4]([CH3:7])([CH3:6])[CH3:5].[C:8]1(=[O:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl-].[NH4+]>C1COCC1>[CH3:5][Si:4]([CH2:3][C:8]1([OH:14])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1)([CH3:7])[CH3:6]

Participants

6

Reactant 4

HCID 7967CyclohexanoneHCID 25517Ammonium ChlorideHCID 75361Silane, (chloromethyl)trimethyl-HCID 5462224Magnesium

Product 1

HCID 4128986HCID 4128986, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A flask was charged with 27.9 g of magnesium and 250 ml of THF, to which a solution of 135 g of chloromethyltrimethylsilane diluted with 150 ml of THF was added dropwise at 50° C. The addition was followed by one hour of stirring at 65° C., after which 98.1 g of cyclohexanone 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 141.6 g (yield 76%) of 1-trimethylsilylmethylcyclohexanol.

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-ed98056e3a164785a0a1075410ae79bc
Source dataset
uspto-grants-2004_08
Patent number
US06780563B2

Reaction notes

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