Tetrabutylammonium Fluoride → HCID 136343240, compound

HRID 860575Notes

Reaction equation

HRID 860575 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([C:25]4[N:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27][CH:26]=4)[CH:14]=[CH:15][C:16]=3[O:17][Si](C(C)(C)C)(C)C)[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[C:1]12([C:11]3[CH:12]=[C:13]([C:25]4[N:30]=[CH:29][C:28]([CH:31]=[O:32])=[CH:27][CH:26]=4)[CH:14]=[CH:15][C:16]=3[OH:17])[CH2:2][CH:3]3[CH2:9][CH:7]([CH2:6][CH:5]([CH2:4]3)[CH2:10]1)[CH2:8]2

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86596051HCID 86596051, compound

Product 1

HCID 136343240HCID 136343240, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of 6-[3-(1-adamantyl)-4-t-butyldimethylsilanyloxyphenyl]-pyridin-3-carboxaldehyde (24.673 g, 0.0511 mol) in 330 mL of dry THF cooled to 0° C. was added dropwise 60.6 mL of 1.0 M solution of tetrabutylammonium fluoride in THF. After 10 minutes from the completion of the addition, the dark red solution was partitioned between EtOAc and 1 M HCl. The mixture was separated the organics were washed with brine, dried (MgSO4), filtered and evaporated. The resulting solid was dried under high vacuum to give 6-[3-(1-adamantyl)-4-hydroxy-phenyl]-pyridin-3-carboxaldehyde (100%). 1H NMR (300 MHz; CDCl3): δ 1.79 (brs, 6H), [2.09 (brs), 2.20 (s), 9 H], 6.47 (brs, 1H), 6.86 (d, J=8.1 Hz, 1H), 7.76 (dd, J1=8.1, J2=2.4 Hz, 1H), 8.01 (d, J=2.4 Hz, 1H), 8.17 (dd, J1=8.1, J2=2.4 Hz, 1H), 9.06 (d, J=2.4 Hz, 1H), 10.09 (s, 1H).

Workup

  1. additionAfter 10 minutes from the completion of the addition
  2. customthe dark red solution was partitioned between EtOAc and 1 M HCl
  3. customThe mixture was separated the
  4. washorganics were washed with brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. customThe resulting solid was dried under high vacuum

Sources & evidence

ORD record
ord-f2e07f170bcd4047ae32d4992d5b08a7
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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