Hexane → HCID 23166912, compound

HRID 1087735Notes

Reaction equation

HRID 1087735 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](/[CH:24]=[CH:25]/[CH:26]([OH:35])[CH2:27][CH:28]([OH:34])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:10]([CH:21]([CH3:23])[CH3:22])[N:11]3[N:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=23)=[CH:4][CH:3]=1.CCCCCC>C(OCC)C.[O-2].[O-2].[Mn+4]>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](/[CH:24]=[CH:25]/[C:26](=[O:35])[CH2:27][CH:28]([OH:34])[CH2:29][C:30]([O:32][CH3:33])=[O:31])=[C:10]([CH:21]([CH3:23])[CH3:22])[N:11]3[N:20]=[CH:19][C:18]4[C:13](=[CH:14][CH:15]=[CH:16][CH:17]=4)[C:12]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 8058HexaneHCID 23166913HCID 23166913, compound

Product 1

HCID 23166912HCID 23166912, compoundYield 51.2%

Reagents, catalysts & solvents 2

HCID 178418406HCID 178418406, compoundCatalystHCID 3283Diethyl EtherSolvent2×

Procedure

A solution of methyl (E)-7-{1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]phthalazin-2-yl}-3,5-dihydroxyhept-6-enoate (3.16 g) in anhydrous diethyl ether (100 ml) was treated with activated manganese dioxide (12.61 g) and the mixture was stirred at room temperature under an argon atmosphere with the exclusion of light for 18 hours. The mixture was then filtered through diatomaceous earth. The filter pad was washed with diethyl ether (2×150 ml) and the combined filtrate and washings were concentrated to give an orange foam. This foam was subjected to flash chromatography on silica gel, using a mixture of diethyl ether and hexane (4:1 v/v) as eluant, to give methyl (E)-7-{1-(4-fluorophenyl)-3-isopropylpyrrolo[2,1-a]phthalazin-2-yl)-3-hydroxy-5-oxohept-6-enoate (1.61 g), in the form of an orange foam. [NMR (in CDCl3): 1.59 (6H, d, J=8 Hz), 2.55 (4 H, m), 3.45-4.15 (5 H, m), 4.40 (1H, m), 5.82 (1H, d, J=16 Hz), 7.05-7.70 (8H, m), 7.85 (1H, d, J=16 Hz), 8.30 (1H, s)].

Workup

  1. filtrationThe mixture was then filtered through diatomaceous earth
  2. washThe filter pad was washed with diethyl ether (2×150 ml)
  3. concentrationthe combined filtrate and washings were concentrated
  4. customto give an orange foam

Sources & evidence

ORD record
ord-ca27514770444fa8ae482e92910b7f46
Source dataset
uspto-grants-1990_10
Patent number
US04960775

Reaction notes

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