Ammonium Chloride → 1-Benzenesulfonyl-2-(2-ethoxycarbonylfuran-5-yl-hydroxymethyl)-5-methylthioindole

HRID 1814120Notes

Reaction equation

HRID 1814120 reaction equation
[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[CH:11]2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:21]([C:23]1[O:27][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:24]=1)=[O:22].[Cl-].[NH4+]>O1CCCC1.C([Li])CCC>[C:1]1([S:7]([N:10]2[C:18]3[C:13](=[CH:14][C:15]([S:19][CH3:20])=[CH:16][CH:17]=3)[CH:12]=[C:11]2[CH:21]([C:23]2[O:27][C:26]([C:28]([O:30][CH2:31][CH3:32])=[O:29])=[CH:25][CH:24]=2)[OH:22])(=[O:9])=[O:8])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

6

Reactant 3

HCID 25517Ammonium ChlorideHCID 15589950Ethyl 5-formylfuran-2-carboxylateHCID 225044271-Benzenesulfonyl-5-methylthioindole

Product 1

HCID 225044401-Benzenesulfonyl-2-(2-ethoxycarbonylfuran-5-yl-hydroxymethyl)-5-methylthioindoleYield 73.7%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 178418339ButyllithiumSolvent

Procedure

To a solution of 1-benzenesulfonyl-5-methylthioindole (0.5178 g) in tetrahydrofuran (17 ml), n-butyl lithium (1.3 ml, 1.59 M) was added dropwise at −78° C. and the mixture was stirred for 30 minutes, followed by addition of the compound obtained in Example 30 (1) (0.3444 g), and the mixture was stirred at −50° C. for 40 minutes. The reaction solution was poured into a saturated aqueous ammonium chloride solution and extracted with ethyl acetate. The organic layer was washed with a saturated aqueous NaCl solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The resulting residue was separated using silica gel column chromatography (hexane:ethyl acetate=1:1) to obtain 0.593 g of the desired product.

Workup

  1. stirringthe mixture was stirred at −50° C. for 40 minutes
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with a saturated aqueous NaCl solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under reduced pressure
  7. customThe resulting residue was separated

Sources & evidence

ORD record
ord-4b90ed32dac44c1bbe0af0bddf0dc37c
Source dataset
uspto-grants-2005_04
Patent number
US06875770B2

Reaction notes

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