Allyl bromide → HCID 14772398, compound

HRID 2073710Notes

Reaction equation

HRID 2073710 reaction equation
[N:1]1[O:2][C:3]2[CH2:4][CH2:5][CH2:6][CH:7]3[C:16]=2[C:15]=1[C:14]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[NH:8]3.[CH2:17](Br)[CH:18]=[CH2:19].C([O-])([O-])=O.[K+].[K+]>CC(C)=O>[CH2:19]([N:8]1[CH:7]2[C:16]3=[C:3]([O:2][N:1]=[C:15]3[C:14]3[CH:13]=[CH:12][CH:11]=[CH:10][C:9]1=3)[CH2:4][CH2:5][CH2:6]2)[CH:18]=[CH2:17]

Participants

5

Reactant 3

HCID 7841Allyl bromide2×HCID 11430Potassium CarbonateHCID 135618014HCID 135618014, compound

Product 1

HCID 14772398HCID 14772398, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
90 °C

Procedure

In 20 ml dry dimethylformaldehyde (DMF) were combined 4.00 g 4,5,5a,6-tetrahydro-3H-isoxazolo[5,4,3-kl]acridine, 3.26 ml allyl bromide and 8 g milled K2CO3. The mixture was heated at 90° C. and mechanically stirred. Every hour 2 ml more allyl bromide was added. After 3 hours, the reaction was complete as observed by TLC. The mixture was partitioned between water and EtOAc. The EtOAc layer was concentrated to a solid which was purified by passing over a silica column (flash chromatography). The product obtained in this manner was recrystallized twice from 20% EtOAc/hexanes to yield 2.99 g solid which was dried in vacuo, m.p. 114°-117° C.

Workup

  1. customThe mixture was partitioned between water and EtOAc
  2. concentrationThe EtOAc layer was concentrated to a solid which
  3. customwas purified
  4. customThe product obtained in this manner
  5. customwas recrystallized twice from 20% EtOAc/hexanes

Sources & evidence

ORD record
ord-08a28a32f03941469958c841ef32fcc8
Source dataset
uspto-grants-1990_04
Patent number
US04920117

Reaction notes

Loading…