Aluminium lithium hydride → HCID 56948669, compound

HRID 1511899Notes

Reaction equation

HRID 1511899 reaction equation
[NH2:1][C:2]1([C:21](O)=[O:22])[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=2)[O:4][CH2:3]1.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[NH2:1][C:2]1([CH2:21][OH:22])[CH2:6][CH:5]([C:7]2[CH:12]=[CH:11][C:10]([CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[CH:9][CH:8]=2)[O:4][CH2:3]1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57554678HCID 57554678, compound

Product 1

HCID 56948669HCID 56948669, compoundYield 42.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3-Amino-5-(4-octylphenyl)tetrahydrofuran-3-carboxylic acid (0.246 g, 0.770 mmol) was dissolved in THF (15.40 ml). A solution of lithium aluminum hydride (0.770 ml, 1.540 mmol) (Aldrich) was added carefully and the reaction stirred for about 3 h. The reaction was quenched by addition of water (60 uL) and stirred for about 30 min. 10% NaOH (180 uL) was added and the reaction stirred for about 1 h. Finally, water (60 uL) was added and the reaction stirred overnight. The mixture was filtered through Celite® and the solvents removed under reduced pressure. The residue was purified by flash column chromatography (0.5″×7″ of silica) eluting with 10% MeOH in methylene chloride and the product fractions combined. The solvents were removed under reduced pressure to provide (3-amino-5-(4-octylphenyl)tetrahydrofuran-3-yl)methanol (0.1 g, 0.327 mmol, 42.5% yield) as a colorless oil: LC/MS (method A) Rt=3.12 min.; MS m/z: 306.42 (M+H)+.

Workup

  1. customThe reaction was quenched by addition of water (60 uL)
  2. stirringstirred for about 30 min
  3. addition10% NaOH (180 uL) was added
  4. stirringthe reaction stirred for about 1 h
  5. additionFinally, water (60 uL) was added
  6. stirringthe reaction stirred overnight
  7. filtrationThe mixture was filtered through Celite®
  8. customthe solvents removed under reduced pressure
  9. customThe residue was purified by flash column chromatography (0.5″×7″ of silica)
  10. washeluting with 10% MeOH in methylene chloride
  11. customThe solvents were removed under reduced pressure

Sources & evidence

ORD record
ord-eb6fda4528ea408bbf211bcaa0f4db9d
Source dataset
uspto-grants-2012_07
Patent number
US08217027B2

Reaction notes

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