1-Bromopropane → HCID 13871882, compound

HRID 1872329Notes

Reaction equation

HRID 1872329 reaction equation
[Mg].Br[CH2:3][CH2:4][CH3:5].Cl[C:7]([CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13])=[O:8].[Cl-].[NH4+]>C1COCC1>[O:8]=[C:7]([CH2:3][CH2:4][CH3:5])[CH2:9][CH2:10][CH2:11][C:12]([O:14][CH3:15])=[O:13]

Participants

6

Reactant 4

HCID 78401-Bromopropane2×HCID 25517Ammonium ChlorideHCID 73916Methyl 4-chloroformylbutyrateHCID 5462224Magnesium

Product 1

HCID 13871882HCID 13871882, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2.82 g of magnesium is introduced into a 250 ml reaction vessel under a nitrogen atmosphere. It is covered with THF and 1 ml of 1-bromopropane is poured in. When the reaction starts, a solution of 9.9 ml of 1-bromopropane in 150 ml of THF is added dropwise over 1.5 hours. Once addition is complete, agitation is carried out for 10 minutes, then the reaction medium is taken to reflux for 3 hours followed by bringing to a temperature of -80° C. A solution of 17 ml of methyl 4-(chloroformyl)butyrate is added very slowly over 45 minutes. Agitation is then carried out for 1 hour at -70° C., then the reaction medium is allowed to return very slowly to 18° C. (over 17 hours). The reaction medium is treated by adding 160 ml of a saturated aqueous solution of ammonium chloride. Agitation is carried out for 30 minutes followed by decanting and re-extraction of the aqueous phase with 100 ml of ether. The organic phases are concentrated. The residue is taken up in 200 ml of ether, then washed twice with 100 ml of water followed by drying over magnesium sulphate and concentration with a rotary evaporator. In this way, 20.2 g of an oil corresponding to the expected product is obtained.

Workup

  1. additionis poured in
  2. additionOnce addition
  3. temperatureto reflux for 3 hours
  4. customby bringing to a temperature of -80° C
  5. waitAgitation is then carried out for 1 hour at -70° C.
  6. customto return very slowly to 18° C.
  7. custom(over 17 hours)
  8. additionThe reaction medium is treated
  9. waitAgitation is carried out for 30 minutes
  10. customby decanting
  11. extractionre-extraction of the aqueous phase with 100 ml of ether
  12. concentrationThe organic phases are concentrated
  13. washwashed twice with 100 ml of water
  14. dry with materialby drying over magnesium sulphate and concentration with a rotary evaporator

Sources & evidence

ORD record
ord-2a4af95130d242d69db43e23734c3703
Source dataset
uspto-grants-2000_08
Patent number
US06107495

Reaction notes

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