Pyridine → HCID 15044334, compound

HRID 1461571Notes

Reaction equation

HRID 1461571 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)=[O:3].[C:13]([OH:18])([CH2:16][CH3:17])([CH3:15])[CH3:14].N1C=CC=CC=1>ClCCl>[C:2](=[O:3])([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH3:12])=[CH:7][CH:6]=1)[O:18][C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 1049PyridineHCID 64052-Methyl-2-butanolHCID 15917599HCID 15917599, compound

Product 1

HCID 15044334HCID 15044334, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

One hundred ml of dichloromethane and 20.27 g (0.1 mol) of p-methylthiophenyl chloroformate prepared in the same manner as in Example 1 were placed in a flask, and 50 ml of a dichloromethane solution containing 8.15 g (0.1 mol) of tert-amyl alcohol and 8.70 g (0.11 mol) of pyridine was dropped thereto at room temperature. The resulting mixture was then stirred for two hours. The reaction solution was washed with water to remove pyridine hydrochlorate, and the organic layer was concentrated under reduced pressure. Finally excessive pyridine was removed in vacuum whereupon 5.09 g of the desired product, tert-amyl p-methylthiophenyl carbonate was obtained as an oily material (yield 100%).

Workup

  1. customwere placed in a flask
  2. additionwas dropped
  3. customat room temperature
  4. washThe reaction solution was washed with water
  5. customto remove pyridine hydrochlorate
  6. concentrationthe organic layer was concentrated under reduced pressure
  7. customFinally excessive pyridine was removed in vacuum whereupon 5.09 g of the desired product

Sources & evidence

ORD record
ord-fee47fec55a34e968a093ad95c9650f5
Source dataset
uspto-grants-1991_12
Patent number
US05075476

Reaction notes

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