Tetrahydrofuran → HCID 21478661, compound

HRID 2292512Notes

Reaction equation

HRID 2292512 reaction equation
[CH3:1][C:2]1[N:6]2[C:7]3[CH:39]=[CH:38][CH:37]=[CH:36][C:8]=3[N:9]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:21][CH2:20][N:19]([CH:22]([C:29]4[CH:34]=[CH:33][C:32]([Cl:35])=[CH:31][CH:30]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:18][CH2:17]3)[C:10](=O)[CH2:11][C:5]2=[N:4][N:3]=1.O1CCCC1.[H-].[Al+3].[Li+].[H-].[H-].[H-].C(OCC)(=O)C>O>[CH3:1][C:2]1[N:6]2[C:7]3[CH:39]=[CH:38][CH:37]=[CH:36][C:8]=3[N:9]([CH2:13][CH2:14][CH2:15][N:16]3[CH2:17][CH2:18][N:19]([CH:22]([C:29]4[CH:30]=[CH:31][C:32]([Cl:35])=[CH:33][CH:34]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:20][CH2:21]3)[CH2:10][CH2:11][C:5]2=[N:4][N:3]=1

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8857Ethyl AcetateHCID 21226445Aluminium lithium hydride2×HCID 21478555HCID 21478555, compound

Product 1

HCID 21478661HCID 21478661, compoundYield 28%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 1.1 g of the compound of Example 211, 20 ml of tetrahydrofuran is added and then 0.17 g of lithium aluminum hydride is added. The resulting mixture is heated to reflux for 30 minutes. To the resultant, 0.82 g of lithium aluminum hydride is added and the mixture is heated to reflux for 20 minutes. To the resulting mixture, ethyl acetate and water are added and the precipitate is removed by filtration using Celite. The filtrate is condensed and purified by silica gel column chromatography (ethyl acetate:methanol=7:1-6:1) to obtain 0.30 g of (213).

Workup

  1. temperatureThe resulting mixture is heated
  2. temperatureto reflux for 30 minutes
  3. temperaturethe mixture is heated
  4. temperatureto reflux for 20 minutes
  5. customthe precipitate is removed by filtration
  6. customcondensed
  7. custompurified by silica gel column chromatography (ethyl acetate:methanol=7:1-6:1)

Sources & evidence

ORD record
ord-cabae8273011475b9b65e9f8ed64d214
Source dataset
uspto-grants-1997_11
Patent number
US05683998

Reaction notes

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