Aluminium lithium hydride → HCID 22221614, compound

HRID 1836040Notes

Reaction equation

HRID 1836040 reaction equation
CON(C)[C:4]([C:6]1[C:14]2[O:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=3)=[CH:11][C:10]=2[CH:9]=[C:8]([OH:22])[CH:7]=1)=[O:5].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[OH:22][C:8]1[CH:7]=[C:6]([CH:4]=[O:5])[C:14]2[O:13][C:12]([C:15]3[CH:16]=[CH:17][C:18]([OH:21])=[CH:19][CH:20]=3)=[CH:11][C:10]=2[CH:9]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 23517375HCID 23517375, compound

Product 1

HCID 22221614HCID 22221614, compoundYield 51%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a cooled (0° C) solution of 119 (0.18 g, 0.58 mmol) in THF (10 ml) was added LiAlH4 (1.5 ml of 1.0M in THF) dropwise. After stirring for 30 min, the reaction was quenched with 2N HCl and partitioned between 2N HCl and EtOAc. The EtOAc was separated, dried, and concentrated. The product was purified by column chromatography on silica gel (30% EtOAc/Hex) to give 120 as a yellow solid (0.075 g, 51%); Mp=261-263° C.; 1H NMR (DMSO-d6) δ 10.36 (s,1 H), 9.79 (s, 1 H), 9.77 (s, 1 H), 7.76 (d, 2 H, J=8.5 Hz), 7.25 (d, 1 H, J=2.0 Hz), 7.17 (s, 1 H), 7.12 (d, 1 H, J=2.1 Hz), 6.88 (d, 2 H, J=8.5 Hz); MS 255 (M+H)+

Workup

  1. customthe reaction was quenched with 2N HCl
  2. custompartitioned between 2N HCl and EtOAc
  3. customThe EtOAc was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe product was purified by column chromatography on silica gel (30% EtOAc/Hex)

Sources & evidence

ORD record
ord-2683c672231f4d4db75c5d96f1c3df96
Source dataset
uspto-grants-2004_08
Patent number
US06774248B2

Reaction notes

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