Tetrabutylammonium Fluoride → 2-Hydroxymethyl-6-phenylpyridine

HRID 1901116Notes

Reaction equation

HRID 1901116 reaction equation
[O:1]([CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:21]=1)[Si](C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[N+](CCCC)(CCCC)(CCCC)CCCC.[F-]>C1COCC1>[OH:1][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[C:22]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:21]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 233701892-(tert-Butyldiphenylsiloxy)methyl-6-phenylpyridine

Product 1

HCID 107261862-Hydroxymethyl-6-phenylpyridine

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 2-(tert-butyldiphenylsiloxy)methyl-6-phenylpyridine (1.2 g) in THF (20 mL) was added Bu4NF (3.3 mL of a 1M solution in THF). After 1 h, NH4OAc buffer was added and the mixture extracted with EtOAc. The organics were dried (MgSO4), concentrated and chromatographed (silica gel; hexane/EtOAc acetate (3:2)) to provide the title compound as a solid.

Workup

  1. extractionthe mixture extracted with EtOAc
  2. dry with materialThe organics were dried (MgSO4)
  3. concentrationconcentrated
  4. customchromatographed (silica gel; hexane/EtOAc acetate (3:2))

Sources & evidence

ORD record
ord-484000312709410baee010375debdbdf
Source dataset
uspto-grants-1996_11
Patent number
US05576338

Reaction notes

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