Water → 2-(3-Hydroxy-1,2,3,4-tetrahydronaphthalenyl)-pyridine

HRID 46503Notes

Reaction equation

HRID 46503 reaction equation
[O:1]1[CH:11]2[CH:2]1[CH2:3][C:4]1[C:9]([CH2:10]2)=[CH:8][CH:7]=[CH:6][CH:5]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Li].O>CCOCC>[OH:1][CH:11]1[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH:3]([C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][N:12]=2)[CH2:2]1

Participants

5

Reactant 3

HCID 962WaterHCID 108880512,3-Epoxy-1,2,3,4-tetrahydronaphthaleneHCID 178506720HCID 178506720, compound

Product 1

HCID 203873802-(3-Hydroxy-1,2,3,4-tetrahydronaphthalenyl)-pyridine

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
-20 °C

Procedure

A solution of 25 g of 2,3-epoxy-1,2,3,4-tetrahydronaphthalene in 250 ml ether is added to a solution of 2-pyridyl lithium (prepared from 2-bromopyridine and butyllithium) cooled to -20° C. After addition, the mixture is allowed to come to room temperature over several hours, then cooled again and treated with water. The separated, dried organics are taken to dryness, and the product purified by chromatography in neutral alumina.

Workup

  1. additionAfter addition
  2. waitto come to room temperature over several hours
  3. temperaturecooled again
  4. customthe product purified by chromatography in neutral alumina

Sources & evidence

ORD record
ord-e020e1f78509438189a408ee230a55d1
Source dataset
uspto-grants-1979_11
Patent number
US04173640

Reaction notes

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