Sodium Hydroxide → (1s,3s)-3-Phenylcyclobutanol

HRID 237292Notes

Reaction equation

HRID 237292 reaction equation
[C:1]1([CH:7]2[CH2:10][C:9](=[O:11])[CH2:8]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].[OH-].[Na+]>C1COCC1>[C:1]1([CH:7]2[CH2:8][CH:9]([OH:11])[CH2:10]2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 1429633-PhenylcyclobutanoneHCID 21226445Aluminium lithium hydride

Product 1

HCID 21876130(1s,3s)-3-PhenylcyclobutanolYield 78.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To the solution of 3-phenyl-cyclobutanone (100 mg) in THF (10 mL) was added LiAlH4 (0.2 mL, 2M in THF). The mixture was stirred at rt for 2 h, then 2M NaOH (1 mL) was added. The organic layer was concentrated and purified by PTLC providing the title compound (80 mg).

Workup

  1. concentrationThe organic layer was concentrated
  2. custompurified by PTLC

Sources & evidence

ORD record
ord-6169a1c02ff847ff96bc0a3a677f9b64
Source dataset
uspto-grants-2014_02
Patent number
US08642583B2

Reaction notes

Loading…