Diisobutylaluminumhydride → HCID 23047463, compound

HRID 2107084Notes

Reaction equation

HRID 2107084 reaction equation
[H-].C([Al+]CC(C)C)C(C)C.[CH:11]([C:14]1[N:18]2[CH:19]=[CH:20][C:21]3[C:26]([C:17]2=[C:16]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:15]=1/[CH:33]=[CH:34]/[C:35](OCC)=[O:36])=[CH:25][CH:24]=[CH:23][CH:22]=3)([CH3:13])[CH3:12]>C1(C)C=CC=CC=1.O1CCCC1>[CH:11]([C:14]1[N:18]2[CH:19]=[CH:20][C:21]3[C:26]([C:17]2=[C:16]([C:27]2[CH:28]=[CH:29][CH:30]=[CH:31][CH:32]=2)[C:15]=1[CH2:33]/[CH:34]=[CH:35]/[OH:36])=[CH:25][CH:24]=[CH:23][CH:22]=3)([CH3:13])[CH3:12]

Participants

5

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86744005HCID 86744005, compound

Product 1

HCID 23047463HCID 23047463, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

A solution of diisobutyl aluminium hydride in toluene (1.5M; 16.8 ml) was added dropwise to a stirred solution of ethyl (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)propenoate (2.4 g) in dry tetrahydrofuran (50 ml) at 0° C. under an atmosphere of argon. The mixture was stirred at 0° C. for 30 minutes and then the reaction mixture was quenched by the dropwise addition of saturated aqueous sodium sulphate solution (50 ml) at 0° C. The resulting gel was then allowed to warm to 20° C. and it was then treated with sufficient aqueous hydrochloric acid (2N) to dissolve the gel. The organic phase was separated and the aqueous phase was extracted with diethyl ether (50 ml). The organic solutions were combined, washed with brine, dried over magnesium sulphate and evaporated, to give (E)-3-(3-isopropyl1-phenylpyrrolo[2,1-a]isoquinolin-2-yl)propen-1-ol in the form of an orange oil (2.14 g).

Workup

  1. customthe reaction mixture was quenched by the dropwise addition of saturated aqueous sodium sulphate solution (50 ml) at 0° C
  2. temperatureto warm to 20° C.
  3. additionit was then treated with sufficient aqueous hydrochloric acid (2N)
  4. dissolutionto dissolve the gel
  5. customThe organic phase was separated
  6. extractionthe aqueous phase was extracted with diethyl ether (50 ml)
  7. washwashed with brine
  8. dry with materialdried over magnesium sulphate
  9. customevaporated

Sources & evidence

ORD record
ord-c35b8bcb4876447598a2b86d6049641c
Source dataset
uspto-grants-1990_06
Patent number
US04933350

Reaction notes

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