Triethylamine → 5-(2-Ethyl-[1,3]dioxolan-2-yl)-2-thienylmethyl methanesulphonate

HRID 49328Notes

Reaction equation

HRID 49328 reaction equation
[CH2:1]([C:3]1([C:8]2[S:12][C:11]([CH2:13][OH:14])=[CH:10][CH:9]=2)[O:7][CH2:6][CH2:5][O:4]1)[CH3:2].C(N(CC)CC)C.[CH3:22][S:23](Cl)(=[O:25])=[O:24].[Cl-].[NH4+]>ClCCl>[CH3:22][S:23]([O:14][CH2:13][C:11]1[S:12][C:8]([C:3]2([CH2:1][CH3:2])[O:4][CH2:5][CH2:6][O:7]2)=[CH:9][CH:10]=1)(=[O:25])=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 31297Methanesulfonyl chlorideHCID 17934796[5-(2-Ethyl-[1,3]dioxolan-2-yl)-2-thienyl]methanol

Product 1

HCID 206363015-(2-Ethyl-[1,3]dioxolan-2-yl)-2-thienylmethyl methanesulphonate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

9.25 g (43.2 mmol) of [5-(2-ethyl-[1,3]dioxolan-2-yl)-2-thienyl]methanol are dissolved in 500 mL of dichloromethane and cooled to 0° C. 9.0 mL (64.7 mmol) of triethylamine are added, followed by 3.5 mL of methylsulphonyl chloride (45.3 mmol). After stirring for 1 hour, the reaction medium is treated with ammonium chloride solution and extracted with dichloromethane. The organic phases are combined, dried and concentrated under reduced pressure. A brown oil is obtained (m=9.28 g; Y=75%).

Workup

  1. extractionextracted with dichloromethane
  2. customdried
  3. concentrationconcentrated under reduced pressure
  4. customA brown oil is obtained (m=9.28 g; Y=75%)

Sources & evidence

ORD record
ord-1df85117b94e458c8d44dd2cbc29df2c
Source dataset
uspto-grants-2004_03
Patent number
US06706725B1

Reaction notes

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