Thionyl Chloride → HCID 66993584, compound

HRID 251608Notes

Reaction equation

HRID 251608 reaction equation
O=S(Cl)Cl.[CH2:5]([C:7]1[CH:12]=[CH:11][CH:10]=[C:9]([CH2:13][CH3:14])[C:8]=1[C:15]1[N:20]=[CH:19][C:18]([C:21](O)([CH2:25][CH2:26][CH3:27])[CH2:22][CH2:23][CH3:24])=[C:17]([O:29][CH3:30])[CH:16]=1)[CH3:6]>N1C=CC=CC=1>[CH2:13]([C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([CH2:5][CH3:6])[C:8]=1[C:15]1[CH:16]=[C:17]([O:29][CH3:30])[C:18]([C:21]([CH2:25][CH2:26][CH3:27])=[CH:22][CH2:23][CH3:24])=[CH:19][N:20]=1)[CH3:14]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 59678326HCID 59678326, compound

Product 1

HCID 66993584HCID 66993584, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

SOCl2 (0.5 mL) is added to a solution of 4-[6-(2,6-diethyl-phenyl)-4-methoxy-pyridin-3-yl]-heptan-4-ol in anhydrous pyridine (5 mL) at 0° C. under nitrogen. The resulting mixture is stirred at room temperature overnight. The volatile materials are removed in vacuo. The residue is treated with water (5 mL), aqueous Na2CO3 (5 mL), and ether. The organic layer is separated and the aqueous is extracted with ether (2×10 mL). The combined extract is washed with brine, dried, and concentrated in vacuo. The crude is purified by PTLC (8:1 hexane/EtOAc) to give 2-(2,6-diethyl-phenyl)-4-methoxy-5-(1-propyl-but-1-enyl)-pyridine. 1H NMR (CDCl3) 8.26 (s, 1H), 7.29 (t, 1H), 7.16 (d, 2H), 6.72 (s, 1H), 5.55 (t, 1H), 3.82 (s, 1H), 2.22-2.37 (m, 8H), 1.30 (m, 2H), 0.87-1.10 (m, 9H).

Workup

  1. customThe volatile materials are removed in vacuo
  2. additionThe residue is treated with water (5 mL), aqueous Na2CO3 (5 mL), and ether
  3. customThe organic layer is separated
  4. extractionthe aqueous is extracted with ether (2×10 mL)
  5. extractionThe combined extract
  6. washis washed with brine
  7. customdried
  8. concentrationconcentrated in vacuo
  9. customThe crude is purified by PTLC (8:1 hexane/EtOAc)

Sources & evidence

ORD record
ord-13f8aff5a61d46288268693b980b10ab
Source dataset
uspto-grants-2011_01
Patent number
US07863454B2

Reaction notes

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