1,4-Dibromobutane → HCID 21896329, compound

HRID 719064Notes

Reaction equation

HRID 719064 reaction equation
[Mg].Br[CH2:3][CH2:4][CH2:5][CH2:6]Br.[O:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]([O:15]CC)=O.[Cl-].[NH4+]>O1CCCC1>[O:8]1[CH2:12][CH2:11][CH2:10][CH:9]1[C:13]1([OH:15])[CH2:6][CH2:5][CH2:4][CH2:3]1

Participants

6

Reactant 4

HCID 80561,4-DibromobutaneHCID 25517Ammonium ChlorideHCID 5462224MagnesiumHCID 10103286ETHYL TETRAHYDRO-2-FUROATE

Product 1

HCID 21896329HCID 21896329, compoundYield 89.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

A flask was charged with 13.6 g of magnesium and 300 ml of tetrahydrofuran, to which 60.3 g of 1,4-dibromobutane was added dropwise at 50° C. After the completion of dropwise addition, the solution was stirred at 60° C. for one hour. To the solution below 40° C., 31.0 g of ethyl tetrahydrofurancarboxylate was added dropwise. The solution was stirred at room temperature for one hour, after which an aqueous solution of ammonium chloride was added for hydrolysis. Ordinary post-treatment yielded 30.2 g of 1-(2-tetrahydrofuranyl)cyclopentanol.

Workup

  1. additionwas added dropwise at 50° C
  2. additionAfter the completion of dropwise addition
  3. stirringThe solution was stirred at room temperature for one hour

Sources & evidence

ORD record
ord-11ceea0086bb4303ad4a745dd0285ed8
Source dataset
uspto-grants-2006_11
Patent number
US07132215B2

Reaction notes

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