Allyl bromide → HCID 59271856, compound

HRID 1893192Notes

Reaction equation

HRID 1893192 reaction equation
[CH:1](NC(C)C)(C)[CH3:2].[CH2:8]([Li])CCC.[CH3:13][O:14][CH:15]([CH3:20])[C:16]([O:18][CH3:19])=[O:17].C(Br)C=C>C1COCC1>[CH3:13][O:14][C:15]([CH3:8])([CH2:20][CH:1]=[CH2:2])[C:16]([O:18][CH3:19])=[O:17]

Participants

6

Reactant 4

HCID 7841Allyl bromideHCID 7912DiisopropylamineHCID 86599Propanoic acid, 2-methoxy-, methyl esterHCID 178418339Butyllithium

Product 1

HCID 59271856HCID 59271856, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-15 °C

Procedure

To a solution of diisopropylamine (2.34 L, 16.4 mol) in THF (6 L) at −48° C. was added n-butyllithium (5.78 L, 14.5 mol) via additional funnel over 35 minutes, and the resulting mixture was warmed to −15° C. over 20 minutes, held at −15° C. for 10 minutes, then cooled down to −40° C. To this solution was added methyl 2-methoxypropionate (1.85 kg, 12.4 mol) via additional funnel over 1.75 hours. After stirring for 30 minutes, allyl bromide (1.4 L, 16.4 mol) was added via additional funnel. The resulting solution was stirred for 30 minutes, warmed to 0° C. over 1 hour, then quenched with 3NHCl (7 L), and extracted with MTBE (2×4 L). The combined organic layers were washed with brine, dried over MgSO4, filtered, and concentrated in vacuo. The crude residue was used in the next reaction without further purification.

Workup

  1. temperaturecooled down to −40° C
  2. stirringThe resulting solution was stirred for 30 minutes
  3. temperaturewarmed to 0° C. over 1 hour
  4. customquenched with 3NHCl (7 L)
  5. extractionextracted with MTBE (2×4 L)
  6. washThe combined organic layers were washed with brine
  7. dry with materialdried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe crude residue was used in the next reaction without further purification

Sources & evidence

ORD record
ord-2814fe917f0d4e9d8cb8b53a7532b3a9
Source dataset
uspto-grants-2013_08
Patent number
US08513234B2

Reaction notes

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