Methanol → HCID 21830649, compound

HRID 1600981Notes

Reaction equation

HRID 1600981 reaction equation
[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7](Cl)(=[O:9])=[O:8])=[CH:3][CH:2]=1.[N:12]1[CH:17]=[CH:16][CH:15]=[C:14]([CH2:18][CH2:19][CH:20]([OH:24])[CH2:21][CH2:22][OH:23])[CH:13]=1.C(N(CC)CC)C.CO>ClCCl>[C:1]1([CH3:11])[CH:6]=[CH:5][C:4]([S:7]([O:23][CH2:22][CH2:21][CH:20]([OH:24])[CH2:19][CH2:18][C:14]2[CH:13]=[N:12][CH:17]=[CH:16][CH:15]=2)(=[O:9])=[O:8])=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 21830683(+/-)-5-(3-Pyridyl)-1,3-pentanediol

Product 1

HCID 21830649HCID 21830649, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Solid para-toluenesulfonyl chloride (1.26 g) was added to a solution of (±)-5-(3-pyridyl)-1,3-pentanediol (1.20 g) and triethylamine (1.11 ml) in anhydrous dichloromethane (20 ml) at -30° C. under nitrogen. The solution was allowed to warm to room temperature over 1 hour and stirring was continued for 24 hours. Methanol (1 ml) was added and the solution concentrated under reduced pressure. The residue was purified by column chromatography over silica eluting with hexane:acetone (3:2) to give the sub-title compound as an oil (1.05 g).

Workup

  1. concentrationthe solution concentrated under reduced pressure
  2. customThe residue was purified by column chromatography over silica eluting with hexane:acetone (3:2)

Sources & evidence

ORD record
ord-d61714cdea6a40caa0fb622831704447
Source dataset
uspto-grants-1999_11
Patent number
US05977105

Reaction notes

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