Tetrahydrofuran → 1-Phenylcyclopentane-1-carbaldehyde

HRID 66264Notes

Reaction equation

HRID 66264 reaction equation
[O:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:6]([Li])[CH2:7][CH2:8][CH3:9]>CCCCCC>[C:3]1([C:4]2([CH:5]=[O:1])[CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:9]=[CH:8][CH:7]=[CH:6][CH:2]=1

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 178418339Butyllithium

Product 1

HCID 110951241-Phenylcyclopentane-1-carbaldehyde

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

In starting the procedure, to a 250 ml (3-necked, round bottom) flask equipped with a nitrogen inlet tube, a rubber septum and a magnetic stirrer is added 100 ml tetrahydrofuran solution of 5.64 g (0.04 mole) of 2, benzyl-4,4,6-tetramethyl- 4,5-dihydro-1,3-oxazine. The mixture is cooled to -78° C and 0.044 mole of normal butyllithium disssolved in hexane is slowly added.

Workup

  1. customto a 250 ml (3-necked, round bottom) flask equipped with a nitrogen inlet tube
  2. additionis slowly added

Sources & evidence

ORD record
ord-8481aa592966435ca1abf8393ba0b713
Source dataset
uspto-grants-1978_12
Patent number
US04131623

Reaction notes

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