3-Pyridinemethanol → HCID 66994286, compound

HRID 1392678Notes

Reaction equation

HRID 1392678 reaction equation
C[Si]([N-][Si](C)(C)C)(C)C.[Na+].[CH3:11][O:12][C:13]([CH2:15]P(OC)(OC)=O)=[O:14].[CH2:22]([C:24]1[CH:29]=[CH:28][CH:27]=[C:26]([CH2:30][CH3:31])[C:25]=1[C:32]1[NH:37][C:36]([CH3:40])(C=O)[CH:35]=[C:34]([CH2:41][CH3:42])[CH:33]=1)[CH3:23].[CH:43]1C=NC=C(CO)C=1.[NH4+].[Cl-]>C1COCC1>[CH3:11][O:12][C:13](=[O:14])[CH:15]=[CH:43][C:35]1[C:36]([CH3:40])=[N:37][C:32]([C:25]2[C:26]([CH2:30][CH3:31])=[CH:27][CH:28]=[CH:29][C:24]=2[CH2:22][CH3:23])=[CH:33][C:34]=1[CH2:41][CH3:42]

Participants

7

Reactant 5

HCID 75103-PyridinemethanolHCID 25517Ammonium ChlorideHCID 80029Trimethyl phosphonoacetateHCID 2724254Sodium bis(trimethylsilyl)amideHCID 86593988HCID 86593988, compound

Product 1

HCID 66994286HCID 66994286, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

Sodium bis(trimethylsilyl)amide (2.9 mL of 1M solution in THF) is added slowly to a solution of trimethyl phosphonoacetate (0.47 mL, 2.9 mmol) in THF (8 mL). The mixture is stirred for 30 minutes at room temperature and then cooled to −78° C. To this is added a solution of 6-(2,6-diethyl-phenyl)-4-ethyl-2-methyl-pyridine-carbaldehyde (813 mg, 2.9 mmol) in THF (5 mL) which is generated from the pyridylmethanol via Swern oxidation. The resulting mixture is stirred for 1.5 hours at ambient temperature, poured into saturated NH4Cl solution, and the layers are separated. The aqueous layer is extracted with EtOAc and the combined organic layers are dried over sodium sulfate and concentrated in vacuo. The residue is purified by flash chromatography (elution with Hex/EtOAc 8:1) to yield 3-[6-(2,6-diethyl-phenyl)-4-ethyl-2-methylpyridin-3-yl]-acrylic acid methyl ester as a pale yellow oil. 1H NMR (CDCl3) 7.91 (d, 1H), 7.29 (m, 2H), 7.18 (d, 2H), 7.01 (s, 1H), 6.10 (d, 1H), 3.83 (s, 3H), 2.72 (q, 2H), 2.60 (s, 3H), 2.34 (m, 4H), 1.21 (t, 3H), 1.04 (m, 6H).

Workup

  1. temperaturecooled to −78° C
  2. stirringThe resulting mixture is stirred for 1.5 hours at ambient temperature
  3. customthe layers are separated
  4. extractionThe aqueous layer is extracted with EtOAc
  5. dry with materialthe combined organic layers are dried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue is purified by flash chromatography (elution with Hex/EtOAc 8:1)

Sources & evidence

ORD record
ord-7917455d17c9470596e001cd54635c41
Source dataset
uspto-grants-2008_03
Patent number
US07342115B2

Reaction notes

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