1,4-Dibromobutane → HCID 23496723, compound

HRID 1836941Notes

Reaction equation

HRID 1836941 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6]Br.[CH3:8][Si:9]([CH3:18])([CH3:17])[CH2:10][CH2:11][C:12]([O:14]CC)=O.[Cl-].[NH4+]>C1COCC1>[CH3:18][Si:9]([CH3:8])([CH3:17])[CH2:10][CH2:11][C:12]1([OH:14])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 25517Ammonium ChlorideHCID 262852Ethyl 3-(trimethylsilyl)propionateHCID 5462224Magnesium

Product 1

HCID 23496723HCID 23496723, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
65 °C

Procedure

A flask was charged with 9.82 g of magnesium and 150 ml of THF, to which a solution of 43.5 g of 1,4-dibromobutane diluted with 50 ml of THF was added dropwise at 50° C. The solution was stirred for one hour at 65° C., after which 23.5 g of ethyl 3-trimethylsilylpropionate was added dropwise below 50° C. The solution was stirred for one hour at room temperature, after which an aqueous solution of ammonium chloride was added for hydrolysis. This was followed by ordinary post-treatments. Upon vacuum distillation, there was obtained 23.6 g (yield 94%) of 1-(2-trimethylsilylethyl)cyclopentanol.

Workup

  1. additionwas added dropwise at 50° C
  2. stirringThe solution was stirred for one hour at room temperature
  3. distillationUpon vacuum distillation

Sources & evidence

ORD record
ord-de3ff53228ae4b359b8c44c999abce55
Source dataset
uspto-grants-2004_08
Patent number
US06780563B2

Reaction notes

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