Aluminium lithium hydride → (2-Phenyl-benzofuran-5-yl)-methanol

HRID 2120589

Reaction equation

HRID 2120589 reaction equation
C[O:2][C:3]([C:5]1[CH:6]=[CH:7][C:8]2[O:12][C:11]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:10][C:9]=2[CH:19]=1)=O.[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1.CCOCC.O.O.O.O.O.O.O.O.O.O.S([O-])([O-])(=O)=O.[Na+].[Na+]>[C:13]1([C:11]2[O:12][C:8]3[CH:7]=[CH:6][C:5]([CH2:3][OH:2])=[CH:19][C:9]=3[CH:10]=2)[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

6

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 66865443Methyl 2-phenylbenzofuran-5-carboxylate

Product 1

HCID 22062820(2-Phenyl-benzofuran-5-yl)-methanolYield 87.6%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 62649Sodium sulfate decahydrateSolvent

Procedure

To a solution of 2-phenyl-benzofuran-5-carboxylic acid methyl ester 27 (0.7 g, 2.8 mmol) in THF (15 ml) was added dropwise a solution of lithium aluminum hydride (1M in THF) (3.6 ml, 3.6 mmol) at 0° C. After the addition, the reaction mixture was allowed to warm to room temperature and stirred for 2 hrs. The mixture was cooled to 0° C., diluted with ether and sodium sulfate decahydrate was added. After filtration the solids were washed with ether, and the organic layer was washed and dried. Evaporation of the solvent and purification by chromatography yielded (2-phenyl-benzofuran-5-yl)-methanol (0.55 g). A mixture of (2-phenyl-benzofuran-5-yl)-methanol (0.5 g, 2.23 mmol), (R)-2-isocyanato-3-phenyl-propionic acid methyl ester 5 (0.55 g, 2.68 mmol), triethylamine (0.74 ml, 5.35 mmol) and THF (15 ml) was heated at 50° C. for 6 hrs. Additional (R) 2-isocyanato-3-phenyl-propionic acid methyl ester 5 (0.15 g) was added, and the mixture was stirred at 50° C. overnight. The solvent was evaporated and the residue was partitioned between ethyl acetate and water. After extraction and evaporation of the solvent, the residue was purified by chromatography to give about 0.76 g of (R)-3-phenyl-2-(2-phenyl-benzofuran-5-ylmethoxycarbonylamino)-propionic acid methyl ester 28.

Workup

  1. additionAfter the addition
  2. temperatureThe mixture was cooled to 0° C.
  3. additionwas added
  4. filtrationAfter filtration the solids
  5. washwere washed with ether
  6. washthe organic layer was washed
  7. customdried
  8. customEvaporation of the solvent and purification by chromatography

Sources & evidence

ORD record
ord-ce33d9053cbc4260a67a09ba6af78c24
Source dataset
uspto-grants-2004_02
Patent number
US06693098B2

Linked notes

Loading…