Triethylamine → HCID 57699683, compound

HRID 1011037Notes

Reaction equation

HRID 1011037 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH:3]([CH2:7][CH2:8][CH2:9][OH:10])[CH2:2]1.C(N(CC)CC)C.[S:18](Cl)([CH3:21])(=[O:20])=[O:19]>ClCCl>[CH3:21][S:18]([O:10][CH2:9][CH2:8][CH2:7][CH:3]1[CH2:4][CH2:5][CH2:6][O:1][CH2:2]1)(=[O:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 576997533-(Oxan-3-yl)propan-1-ol

Product 1

HCID 57699683HCID 57699683, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3-(tetrahydro-2H-pyran-3-yl)-1-propanol (2.64 g) in dry dichloromethane (78 ml) at 0° C. was added triethylamine (6.21 ml) followed by mesyl chloride (1.85 ml). The reaction mixture was allowed to warm to room temperature as the ice melted and allowed to stir for three hours. The reaction mixture was washed with sodium hydrogen carbonate. The organic layer was separated, dried by passing through a hydrophobic frit and concentrated in vacuo. to give a yellow oil (4.42 g). The product was purified by silica chromatography (80 g) (ISCO) using a gradient elution of 0-50% cyclohexane:ethyl acetate to afford the title compound as a clear oil (3.79 g).

Workup

  1. washThe reaction mixture was washed with sodium hydrogen carbonate
  2. customThe organic layer was separated
  3. customdried
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-60610c6ad8384ee69927798524eb3b9e
Source dataset
uspto-grants-2011_07
Patent number
US07977344B2

Reaction notes

Loading…