Pyridine → HCID 18414631, compound

HRID 991582Notes

Reaction equation

HRID 991582 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([C:8]1[CH:31]=[C:30]([CH:32]2[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]2)[CH:29]=[CH:28][C:9]=1[O:10][CH2:11][CH2:12][CH2:13][O:14][C:15]1[CH:16]=[C:17]([CH:25]=[CH:26][CH:27]=1)[CH:18](O)[C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH2:6][CH3:7].N1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:3][CH:18]([C:17]1[CH:25]=[CH:26][CH:27]=[C:15]([O:14][CH2:13][CH2:12][CH2:11][O:10][C:9]2[CH:28]=[CH:29][C:30]([CH:32]3[CH2:37][CH2:36][CH2:35][CH2:34][CH2:33]3)=[CH:31][C:8]=2[CH2:5][CH2:6][CH3:7])[CH:16]=1)[C:19]([O:21][CH2:22][CH3:23])=[O:20]

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 18414624HCID 18414624, compound

Product 1

HCID 18414631HCID 18414631, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Thionyl chloride (0.15 mL) was added to a solution of ethyl 4-(3-(2-propyl-4-cyclohexylphenoxy)propoxy)mandelate of Step C (0.71 g), pyridine (0.19 mL), and toluene (15 mL). The reaction mixture was stirred 6-7 h and then partitioned between ethyl acetate and water. The organic layer was washed twice with water, once with brine, dried over sodium sulfate, and filtered. The solvent was removed in vacuo and the resulting oil was used as such for the next step.

Workup

  1. custompartitioned between ethyl acetate and water
  2. washThe organic layer was washed twice with water, once with brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customThe solvent was removed in vacuo

Sources & evidence

ORD record
ord-05ead6b4fb40403ca5184e3516850025
Source dataset
uspto-grants-2002_10
Patent number
US06465497B2

Reaction notes

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