Aluminium lithium hydride → 3-PHENANTHRENOL, 1,2,3,4,4A,9,10,10A-OCTAHYDRO-4

HRID 1197536Notes

Reaction equation

HRID 1197536 reaction equation
[NH:1]1[C:8]23[CH2:17][CH:4]([CH2:5][CH2:6][CH:7]2[CH2:16][CH2:15][C:14]2[C:9]3=[CH:10][CH:11]=[CH:12][CH:13]=2)[O:3][C:2]1=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[CH3:2][NH:1][C:8]12[C:9]3[C:14](=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:15][CH2:16][CH:7]1[CH2:6][CH2:5][CH:4]([OH:3])[CH2:17]2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydride2×HCID 67820505HCID 67820505, compound

Product 1

HCID 232744943-PHENANTHRENOL, 1,2,3,4,4A,9,10,10A-OCTAHYDRO-4Yield 83%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of the compound from Example 62 (1.4 g, 5.75 mmol) in 20 ml THF was added to a slurry of lithium aluminum hydride (1 g) in 30 ml THF. After stirring overnight, additional lithium aluminum hydride was added (1 g) and stirring continued 3 hours. Workup afforded the title compound as a white solid (1.1 g, 83%), mp 141°-143° C.

Workup

  1. stirringstirring continued 3 hours

Sources & evidence

ORD record
ord-d800dc629c6842959016620750708ad8
Source dataset
uspto-grants-1994_01
Patent number
US05276053

Reaction notes

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