Aluminium lithium hydride → HCID 10295026, compound

HRID 1062593Notes

Reaction equation

HRID 1062593 reaction equation
[CH3:1][N:2]1[C:11]2[C:6](=[CH:7][C:8]([C:12]#[C:13][CH2:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[CH:9][CH:10]=2)[C:5](=[O:21])[N:4]([CH2:22][C:23]2[CH:31]=[CH:30][C:26]([C:27](Cl)=[O:28])=[CH:25][CH:24]=2)[C:3]1=[O:32].[H-].[Al+3].[Li+].[H-].[H-].[H-]>O1CCCC1>[OH:28][CH2:27][C:26]1[CH:25]=[CH:24][C:23]([CH2:22][N:4]2[C:5](=[O:21])[C:6]3[C:11](=[CH:10][CH:9]=[C:8]([C:12]#[C:13][CH2:14][C:15]4[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=4)[CH:7]=3)[N:2]([CH3:1])[C:3]2=[O:32])=[CH:31][CH:30]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 22281864HCID 22281864, compound

Product 1

HCID 10295026HCID 10295026, compoundYield 55.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 0.5 g (1.1 mmol) of compound obtained in Example 19, Step 1 in 50 ml of tetrahydrofuran, was added dropwise to a suspension of 0.047 g (1.2 mmol) lithium aluminum hydride in 50 ml tetrahydrofuran at 0° C. After complete addition, the off-white suspension was warmed to room temperature and stirring was continued for 4 hours. The reaction mixture was concentrated in vacuum and carefully partitioned between 1 M HCl and ethyl acetate. The organic layer was dried over magnesium sulfate, filtered, and concentrated to give an oily yellow solid. Chromatography (silica, 1:1 ethyl acetatelhexanes) gave 0.25 g of the title compound as a white solid.

Workup

  1. additionAfter complete addition
  2. concentrationThe reaction mixture was concentrated in vacuum
  3. customcarefully partitioned between 1 M HCl and ethyl acetate
  4. dry with materialThe organic layer was dried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customto give an oily yellow solid

Sources & evidence

ORD record
ord-3f3b1171abe14460a0e33be5d6930f48
Source dataset
uspto-grants-2005_11
Patent number
US06962922B2

Reaction notes

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