Ammonium Chloride → HCID 68893457, compound

HRID 733017Notes

Reaction equation

HRID 733017 reaction equation
[Cl-].[CH3:2][O:3]C[P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Li][CH2:25][CH2:26][CH2:27][CH3:28].[C:29]1([C:35]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[O:36][CH2:37][C:38]2[N:43]=C(C=O)C=[CH:40][CH:39]=2)[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.[NH4+].[Cl-]>C1COCC1.O>[CH3:2][O:3][CH:25]=[CH:26][C:27]1[CH:28]=[CH:40][CH:39]=[C:38]([CH2:37][O:36][C:35]([C:52]2[CH:57]=[CH:56][CH:55]=[CH:54][CH:53]=2)([C:29]2[CH:30]=[CH:31][CH:32]=[CH:33][CH:34]=2)[C:46]2[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=2)[N:43]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 2723798Methoxymethyl-triphenylphosphonium chlorideHCID 21874751HCID 21874751, compoundHCID 178418339Butyllithium

Product 1

HCID 68893457HCID 68893457, compoundYield 95.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred solution of (methoxymethyl)triphenylphosphonium chloride (2.79 g, 8.13 mmol) in THF (50 mL) at 0° C. was treated dropwise with n-BuLi (1.6-M in hexanes, 5.08 mL, 8.13 mmol), stirred for 1 h, treated with a solution of 6-(triphenylmethoxy)methylpyridine-2-carboxaldehyde (1.54 g, 4.06 mmol) in THF (15 mL) and allowed to warm to room temperature overnight. The reaction was treated with saturated NH4Cl solution (5 mL), diluted with water (50 mL), extracted with EtOAc (2×50 mL) and the combined organic phase diluted with iso-hexane (50 mL), dried (MgSO4), filtered through silica and concentrated in vacuo to give 2-(2-methoxyethenyl)-6-(triphenylmethoxy)methylpyridine (1.58 g) as a yellow oil. A solution of this crude alkene and 10% Pd/C (216 mg, 0.203 mmol) in EtOAc (50 mL) was stirred under a hydrogen atmosphere for 16 h, filtered through Celite and concentrated in vacuo to give the title compound (1.08 g, 65%) as a yellow oil; NMR δH (400 MHz, CDCl3) 7.67-7.64 (1H, m), 7.52-7.49 (6H, m), 7.32-7.21 (10H, m), 7.09-7.07 (1H, m), 4.34 (2H, s), 3.69 (2H, t, J 6.5 Hz), 3.32 (3H, s) and 2.98 (2H, t, J 6.5 Hz); M/Z 410 (M+H)+.

Workup

  1. extractionextracted with EtOAc (2×50 mL)
  2. additionthe combined organic phase diluted with iso-hexane (50 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered through silica
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-1d8459464fb049f2bc07e77e96dfe282
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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