Aluminium lithium hydride → (4-(5-Fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)phenyl)methanol

HRID 1662468Notes

Reaction equation

HRID 1662468 reaction equation
[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:13]([C:14](OC)=[O:15])=[CH:12][C:11]=2[C:20]2([CH:25]=[CH2:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1.C(OCC)C>[F:1][C:2]1[C:3]([C:10]2[CH:19]=[CH:18][C:13]([CH2:14][OH:15])=[CH:12][C:11]=2[C:20]2([CH:25]=[CH2:26])[CH2:24][CH2:23][CH2:22][CH2:21]2)=[CH:4][C:5]([O:8][CH3:9])=[N:6][CH:7]=1

Participants

5

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 57467655Methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)benzoate

Product 1

HCID 57706064(4-(5-Fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)phenyl)methanol

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of methyl 4-(5-fluoro-2-methoxypyridin-4-yl)-3-(1-vinylcyclopentyl)benzoate 66.67E (51.0 mg, 143 μmol) in THF (2.0 mL) was slowly added LAH, (1.0M solution in diethyl ether) (0.30 mL, 287 μmol) at room temperature. The resulting mixture was stirred at 50° C. for 1 hour. Standard work up conditions were employed and the solvent was removed. The desired product was used in the next step without further purification. MS ESI (pos.) m/e: 328.2 (M+H)+.

Workup

  1. customat room temperature
  2. customthe solvent was removed
  3. customThe desired product was used in the next step without further purification

Sources & evidence

ORD record
ord-6c9eb74d71e64ed5b178b7c4a9395394
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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