Aluminium lithium hydride → HCID 22163769, compound

HRID 1087739Notes

Reaction equation

HRID 1087739 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[CH:7]([C:10]1[N:14]2[N:15]=[CH:16][C:17]3[C:22]([C:13]2=[C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[C:11]=1[C:29](OCC)=[O:30])=[CH:21][CH:20]=[CH:19][CH:18]=3)([CH3:9])[CH3:8]>C(OCC)C>[OH:30][CH2:29][C:11]1[C:12]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=[C:13]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[CH:16]=[N:15][N:14]2[C:10]=1[CH:7]([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22163774HCID 22163774, compound

Product 1

HCID 22163769HCID 22163769, compoundYield 58.8%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
0 °C

Procedure

A stirred suspension of lithium aluminium hydride (1.0 g) in diethyl ether (40 ml) at 0° C. under an atmosphere of argon was treated with a solution of ethyl 3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine-2-carboxylate (2.35 g) in diethyl ether (60 ml). The reaction mixture was stirred at 0° C. for 2 hours and then it was quenched by dropwise treatment with ethyl acetate (50 ml). After stirring for a further period of 1 hour it was treated with saturated aqueous sodium sulphate solution (100 ml) and the resulting mixture was then extracted with ethyl acetate (3×100 ml). The combined extract was dried over magnesium sulphate and evaporated and the resulting residue was subjected to flash chromatography on silica gel, using as eluant a mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (3:1 v/v), to give 2-hydroxymethyl-3-isopropyl-1-phenylpyrrolo[2,1-a]phthalazine (1.22 g) in the form of a yellow gummy solid. [NMR (in a mixture of CDCl3 and D2O): 1.57 (6H, d, J=7 Hz), 3.86 (1H, septet, J=7 Hz), 4.62 (2H, s), 7.25-7.53 (8H, m), 7.58-7.64 (1H, m), 8.3 (1H, s); Mass spectrum (electron impact) m/z=316].

Workup

  1. customit was quenched by dropwise treatment with ethyl acetate (50 ml)
  2. stirringAfter stirring for a further period of 1 hour it
  3. additionwas treated with saturated aqueous sodium sulphate solution (100 ml)
  4. extractionthe resulting mixture was then extracted with ethyl acetate (3×100 ml)
  5. extractionThe combined extract
  6. dry with materialwas dried over magnesium sulphate
  7. customevaporated
  8. additiona mixture of petroleum ether (b.p. 40°-60° C.) and diethyl ether (3:1 v/v)

Sources & evidence

ORD record
ord-4e92a5f458034cc4b9067770905aa8f1
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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