3-Pyridinepropanol → HCID 22721404, compound

HRID 1656317Notes

Reaction equation

HRID 1656317 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH:2]=1.[H-].[Na+].C([O:16][C:17]1[C:22]([C:23]([CH3:26])([CH3:25])[CH3:24])=[CH:21][C:20]([CH2:27][CH2:28][CH2:29]OS(C2C=CC(C)=CC=2)(=O)=O)=[CH:19][C:18]=1[C:41]([CH3:44])([CH3:43])[CH3:42])(=O)C>C1COCC1.CN(P(N(C)C)(N(C)C)=O)C>[C:41]([C:18]1[CH:19]=[C:20]([CH2:27][CH2:28][CH2:29][O:10][CH2:9][CH2:8][CH2:7][C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)[CH:21]=[C:22]([C:23]([CH3:26])([CH3:25])[CH3:24])[C:17]=1[OH:16])([CH3:43])([CH3:44])[CH3:42]

Participants

6

Reactant 3

HCID 178613-PyridinepropanolHCID 24758Sodium hydrideHCID 19787830HCID 19787830, compound

Product 1

HCID 22721404HCID 22721404, compoundYield 62%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolvent3×HCID 12679HexamethylphosphoramideSolvent

Procedure

A solution of 3.66 g (26.68 mmol) of 3-(3-pyridyl)propanol in 30 ml anhydrous THF and 3.5 ml dry HMPA is added via syringe to a stirred suspension of 2.56 g (60% oil dispersion, 53.33 mmol) of NaH in 35 ml of anhydrous THF under an inert atmosphere at O° C., followed by a 2 h period at reflux. The sodium alcoholate solution is then recooled to 0° C. and 10.68 g (23.19 mmol) of 3-(4-acetoxy-3,5-di-tert-butylphenyl)-1-(tosyloxy)propane, dissolved in 35 ml of anhydrous THF, is added, fo-Wowed by refluxing for 2 h and stirring overnight at room temperature. After usual workup, the crude product (9.88 g; brown oil) is purified by flash-chromatography over silica gel, eluting with n-hexane/ethyl acetate 3:1, yielding 2.88 g (62% of 2,6-ditert-butyl-4-[7-(3-pyridyl)-4-oxaheptyl]phenol as amber oil. (C25H37NO2 ; F.W. 383.6).

Workup

  1. temperatureat reflux
  2. customis then recooled to 0° C.
  3. additionis added
  4. temperaturefo-Wowed by refluxing for 2 h
  5. customAfter usual workup, the crude product (9.88 g; brown oil) is purified by flash-chromatography over silica gel
  6. washeluting with n-hexane/ethyl acetate 3:1

Sources & evidence

ORD record
ord-529ddb0bd6a744dfb0db86dda7eb1738
Source dataset
uspto-grants-1993_10
Patent number
US05254549

Reaction notes

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