Ammonium Chloride → HCID 68893457, compound

HRID 750543Notes

Reaction equation

HRID 750543 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 5H (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-fc9ad66448104e9f945380d513104757
Source dataset
uspto-grants-2008_07
Patent number
US07405219B2

Reaction notes

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