Diisobutylaluminumhydride → HCID 22163750, compound

HRID 1087741Notes

Reaction equation

HRID 1087741 reaction equation
[CH:1]([C:4]1[N:8]2[N:9]=[CH:10][C:11]3[C:16]([C:7]2=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1/[CH:23]=[CH:24]/[C:25](OCC)=[O:26])=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:3])[CH3:2].[H-].C([Al+]CC(C)C)C(C)C>O1CCCC1>[CH:1]([C:4]1[N:8]2[N:9]=[CH:10][C:11]3[C:16]([C:7]2=[C:6]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:5]=1[CH2:23]/[CH:24]=[CH:25]/[OH:26])=[CH:15][CH:14]=[CH:13][CH:12]=3)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 21225700DiisobutylaluminumhydrideHCID 86744242HCID 86744242, compound

Product 1

HCID 22163750HCID 22163750, compoundYield 125.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred solution of ethyl (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)propenoate (0.86 g) in dry tetrahydrofuran (25 ml) at 0° C. under an atmosphere of argon was treated dropwise with a solution of diisobutyl aluminium hydride in tetrahydrofuran (1M; 6.7 ml). The reaction mixture was stirred at 0° C. for 1 hour and then it was quenched by dropwise treatment with saturated aqueous sodium sulphate solution (25 ml). The resulting mixture was partitioned between water (100 ml) and diethyl ether (100 ml), and the organic layer was separated. The aqueous layer was extracted with diethyl ether (2×100 ml) and the combined organic layers were dried over magnesium sulphate and evaporated, to give (E)-3-(3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazin-2-yl)propen-1-ol (0.96 g), in the form of a yellow oil. [NMR (in a mixture of CDCl3 and D2O ): 1.54 (6H, d, J=7 Hz), 3.82 (1H, septet, J=7 Hz), 4.15 (2H, dd, J=7 Hz, 1 Hz), 5.55 (1H, dt, J=16 Hz, 7 Hz), 6.62 (1H, dt, J=16 Hz, 1 Hz), 7.21-7.32 (3H, m), 7.35-7.62 (6H, m), 8.23 (1H, s)].

Workup

  1. customit was quenched by dropwise treatment with saturated aqueous sodium sulphate solution (25 ml)
  2. customThe resulting mixture was partitioned between water (100 ml) and diethyl ether (100 ml)
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with diethyl ether (2×100 ml)
  5. dry with materialthe combined organic layers were dried over magnesium sulphate
  6. customevaporated

Sources & evidence

ORD record
ord-5dcf644d95cd4a93a0b6e14b00d4a0d7
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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