Pyridine → HCID 14343902, compound

HRID 35755Notes

Reaction equation

HRID 35755 reaction equation
O[CH2:2][CH2:3][C@H:4]1[C:13]([CH3:15])([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:16])[CH:11]=2)[C:6]([CH3:18])([CH3:17])[CH2:5]1.N1C=CC=CC=1.S(Cl)([Cl:27])=O>C1(C)C=CC=CC=1>[Cl:27][CH2:2][CH2:3][C@H:4]1[C:13]([CH3:15])([CH3:14])[C:12]2[C:7](=[CH:8][CH:9]=[C:10]([CH3:16])[CH:11]=2)[C:6]([CH3:18])([CH3:17])[CH2:5]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 14343899(S)-3-(2-hydroxyethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene

Product 1

HCID 14343902HCID 14343902, compoundYield 61.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

(S)-3-(2-Hydroxyethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene ([α]546 -8.1° (C=0.62 in ethanol)) (70.5 g; 0.287 mol) was dissolved in toluene (700 g), and pyridine (25.0 g; 0.316 mol) was added thereto. The resulting mixture was cooled to 0° C., and thionyl chloride (41.0 g; 0.345 mol) was added dropwise thereto. After the addition was completed, the resultant mixture was heated at 60° C. for 5 hours. The reaction mixture was cooled, washed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order, dried over anhydrous sodium sulfate and concentrated to give (S)-3-(2-chloroethyl)-1,1,4,4,6-pentamethyl-1,2,3,4-tetrahydronaphthalene (46.5 g; 0.176 mol; 61%). B.P., 106°-107° C./0.13 mmHg. [α]546 -33.4° (C=1.2 in ethanol).

Workup

  1. additionAfter the addition
  2. temperatureThe reaction mixture was cooled
  3. washwashed with dilute hydrochloric acid, saturated sodium carbonate solution and saturated sodium chloride solution in order
  4. dry with materialdried over anhydrous sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6c5b058519e54a078cb60c8c57c5a48e
Source dataset
uspto-grants-1988_08
Patent number
US04767882

Reaction notes

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