Triethylamine → Methanesulfonic acid 3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl ester

HRID 747197Notes

Reaction equation

HRID 747197 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10]([CH2:12][OH:13])[O:9][N:8]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.[CH3:21][S:22](Cl)(=[O:24])=[O:23].C(=O)(O)[O-].[Na+]>ClCCl>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10]([CH2:12][O:13][S:22]([CH3:21])(=[O:24])=[O:23])[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 17954475[3-(5-Bromothien-2-yl)-4,5-dihydroisoxazol-5-yl]methanol

Product 1

HCID 59749454Methanesulfonic acid 3-(5-bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl esterYield 65.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-yl]-methanol (10.7 g, 40.6 mmol) was added to anhydrous dichloromethane (200 ml) followed by addition of triethylamine (7.9 ml, 56.9 mmol). The solution was cooled to 0° C. followed by dropwise addition of methane sulfonyl chloride (3.8 ml, 48.7 mmol). The reaction was stirred for 2 hours at 0° C. and then aqueous sodium bicarbonate (100 ml) was added. After further extraction with dichloromethane (2×100 ml), the organic layers were combined, dried over sodium sulfate, and concentrated in vacuo to give the desired product (9 g).

Workup

  1. extractionAfter further extraction with dichloromethane (2×100 ml)
  2. dry with materialdried over sodium sulfate
  3. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-090cc0b4da4242e39f5357b4e2d43555
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

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