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p-Toluenesulfonic acid monohydrate → 7-(4,4,4-Trifluoro-3-hydroxy-3-hydroxymethyl-1,1-dimethyl-butyl)-2,3-dihydrobenzofuran-5-sulfonic acid dimethylamide

HRID 400641
Notes
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Reaction equation

HRID 400641 reaction equation
[CH3:1][N:2]([CH3:30])[S:3]([C:6]1[CH:7]=[C:8]([C:15]([CH3:29])([CH3:28])[CH2:16][C:17]2([C:24]([F:27])([F:26])[F:25])[CH2:21][O:20]C(C)(C)[O:18]2)[C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)(=[O:5])=[O:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>CO.C(=O)(O)[O-].[Na+]>[CH3:30][N:2]([CH3:1])[S:3]([C:6]1[CH:7]=[C:8]([C:15]([CH3:28])([CH3:29])[CH2:16][C:17]([OH:18])([CH2:21][OH:20])[C:24]([F:25])([F:27])[F:26])[C:9]2[O:13][CH2:12][CH2:11][C:10]=2[CH:14]=1)(=[O:5])=[O:4]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 600263797-[2-(2,2-Dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethyl-ethyl]-2,3-dihydrobenzofuran-5-sulfonic acid dimethylamide

Product 1

HCID 600266667-(4,4,4-Trifluoro-3-hydroxy-3-hydroxymethyl-1,1-dimethyl-butyl)-2,3-dihydrobenzofuran-5-sulfonic acid dimethylamideYield 78.7%

Reagents, catalysts & solvents 2

HCID 887Methanol
Solvent
HCID 516892Sodium BicarbonateSolvent

Procedure

A mixture of 1.18 g (2.61 mmol) of 7-[2-(2,2-dimethyl-4-trifluoromethyl-[1,3]dioxolan-4-yl)-1,1-dimethyl-ethyl]-2,3-dihydrobenzofuran-5-sulfonic acid dimethylamide and 303 mg (1.59 mmol) of p-toluenesulfonic acid monohydrate in 20 mL of methanol was warmed at reflux for 3 days. The mixture was then cooled and diluted with 15 mL of saturated aqueous sodium bicarbonate and extracted with three 15 mL portions of ethyl acetate. The combined organic layers were washed with two 15 mL portions of saturated aqueous sodium bicarbonate, two 15 mL portions of brine, dried over magnesium sulfate, filtered, and concentrated in vacuo. The residue was triturated with ether to afford 845 mg (78% yield) of the title compound as a white solid.

Workup

  1. temperaturewas warmed
  2. temperatureat reflux for 3 days
  3. temperatureThe mixture was then cooled
  4. extractionextracted with three 15 mL portions of ethyl acetate
  5. washThe combined organic layers were washed with two 15 mL portions of saturated aqueous sodium bicarbonate, two 15 mL portions of brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-2bd1334ff7eb4dc0bb1369bd69ceadd7
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08741897B2

Reaction notes

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