Triethylamine → 1-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane

HRID 1533036Notes

Reaction equation

HRID 1533036 reaction equation
[CH3:1][S:2](Cl)(=[O:4])=[O:3].[Cl:6][C:7]1[CH:8]=[C:9]([CH:14]([CH2:17][CH:18]2[O:22][CH2:21][CH2:20][O:19]2)[CH2:15][OH:16])[CH:10]=[CH:11][C:12]=1[Cl:13].C(N(CC)CC)C>ClCCl>[CH3:1][S:2]([O:16][CH2:15][CH:14]([C:9]1[CH:10]=[CH:11][C:12]([Cl:13])=[C:7]([Cl:6])[CH:8]=1)[CH2:17][CH:18]1[O:19][CH2:20][CH2:21][O:22]1)(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 226137962-(3,4-Dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol

Product 1

HCID 226137911-Methanesulphonyloxy-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propaneYield 101.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

Methanesulphonyl chloride (5.5 g) was added over 10 minutes to an ice-cooled solution of 2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propan-1-ol (12 g) (see Preparation 15) and triethylamine (5.7 g) in dichloromethane (100 ml). The mixture was stirred for 30 minutes before further addition of dichloromethane (50 ml). The solution was then washed sequentially with water (3×50 ml) and brine (50 ml) before drying over anhydrous sodium sulphate. Removal of the solvent under reduced pressure gave 1-methanesulphonyloxy-2-(3,4-dichlorophenyl)-3-(1,3-dioxolan-2-yl)propane as a yellow oil (15.6 g) which solidified upon standing.

Workup

  1. washThe solution was then washed sequentially with water (3×50 ml) and brine (50 ml)
  2. dry with materialbefore drying over anhydrous sodium sulphate
  3. customRemoval of the solvent under reduced pressure

Sources & evidence

ORD record
ord-f282a23de293484bbdbfdd749333145f
Source dataset
uspto-grants-2001_03
Patent number
US06207678B1

Reaction notes

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