Pyridine → HCID 22116707, compound

HRID 1460288Notes

Reaction equation

HRID 1460288 reaction equation
[C:1]([CH:5]1[CH2:10][CH2:9][CH:8]([OH:11])[CH2:7][CH2:6]1)([CH3:4])([CH3:3])[CH3:2].N1C=CC=CC=1.Cl[C:19]([O:21][CH:22]=[CH2:23])=[O:20]>C(Cl)(Cl)Cl>[C:19](=[O:20])([O:21][CH:22]=[CH2:23])[O:11][CH:8]1[CH2:7][CH2:6][CH:5]([C:1]([CH3:4])([CH3:2])[CH3:3])[CH2:10][CH2:9]1

Participants

5

Reactant 3

HCID 1049PyridineHCID 73914-tert-ButylcyclohexanolHCID 78808Vinyl chloroformate

Product 1

HCID 22116707HCID 22116707, compoundYield 50.4%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a 250 mL 3-neck round bottom flask fitted with a magnetic stirrer, condenser, thermometer, ice water bath, dropping funnel, was added 10.0 g (64.0 mmol) of 4-t-butylcyclohexanol, 5.6 g (70.3 mmol) of pyridine and 100 mL of chloroform. The reaction mixture was cooled to less than 10° C. and 6.8 g (64.0 mmol) of vinyl chloroformate was added so that the temperature remained below 15° C. The reaction mixture was stirred at room temperature for 20 hours, then washed with 100 mL 2N HCl, 100 mL distilled water and dried over magnesium sulfate. The solvent was removed on a rotary evaporator and the resulting oil chromatographed (silica gel, methylene chloride) to afford 7.3 g (32.28 mmol, 50.4%) of an oil. FTIR (neat, capillary) 2949.85, 2867.24, 1753.81, 1650.71, 1478.96, 1468.77, 1452.57, 1393.73, 1385.90, 1361.15, 1325.03, 1296.75, 1246.94, 1193.82, 1178.29, 1155.10, 1118.52, 1106.53, 1083.32, 1041.01, 1016.58, 1005.94, 946.14, 923.71, 902.63, 867.23, 843.74, 804.43, 783.98, 758.83, 696.74, 668.14. NMR (CDCl3) δ 6.86-7.22 (1H,m), 4.37-4.97 (2H,m), 1.00-2.30 (10H,m), 0.85 (9H,S). ##STR42##

Workup

  1. customTo a 250 mL 3-neck round bottom flask fitted with a magnetic stirrer, condenser
  2. customthermometer, ice water bath, dropping
  3. temperatureThe reaction mixture was cooled to less than 10° C.
  4. customremained below 15° C
  5. washwashed with 100 mL 2N HCl, 100 mL
  6. distillationdistilled water
  7. dry with materialdried over magnesium sulfate
  8. customThe solvent was removed on a rotary evaporator
  9. customthe resulting oil chromatographed (silica gel, methylene chloride)

Sources & evidence

ORD record
ord-5f582638827947309ba45764a0b0ab67
Source dataset
uspto-grants-1991_12
Patent number
US05070215

Reaction notes

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