Ethanethiol → HCID 11361588, compound

HRID 556775Notes

Reaction equation

HRID 556775 reaction equation
C([O:8][C@@H:9]1[C@@H:14]([O:15]CC2C=CC=CC=2)[C@H:13]([O:23]CC2C=CC=CC=2)[C@@H:12]([CH2:31][O:32]CC2C=CC=CC=2)[O:11][C@H:10]1[C:40]1[CH:56]=[CH:55][C:43]2[S:44][CH:45]=[C:46]([CH2:47][CH2:48][C:49]3[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=3)[C:42]=2[CH:41]=1)C1C=CC=CC=1.C(S)C.C(=O)([O-])[O-].[K+].[K+]>ClCCl>[C:49]1([CH2:48][CH2:47][C:46]2[C:42]3[CH:41]=[C:40]([C@@H:10]4[O:11][C@H:12]([CH2:31][OH:32])[C@@H:13]([OH:23])[C@H:14]([OH:15])[C@H:9]4[OH:8])[CH:56]=[CH:55][C:43]=3[S:44][CH:45]=2)[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1

Participants

5

Reactant 3

HCID 6343EthanethiolHCID 11430Potassium CarbonateHCID 66765654HCID 66765654, compound

Product 1

HCID 11361588HCID 11361588, compoundYield 64.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 5-(2,3,4,6-tetra-O-benzyl-β-D-glucopyranosyl)-3-(2-phenylethyl)benzo[b]thiophene (0.1 g) and ethanethiol (0.16 g) in dichloromethane (6 mL) was added boron trifluoride diethyl ether complex (0.28 g) at room temperature, and the mixture was stirred at room temperature for 3 hours. A saturated potassium carbonate aqueous solution was added to the reaction mixture, and the mixture was extracted with ethylacetate. The organic layer washed with brine and dried over anhydrous magnesium sulfate, and the solvent was removed under reduced pressure. The residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1) to give the title compound (0.034 g).

Workup

  1. additionwas added boron trifluoride diethyl ether complex (0.28 g) at room temperature
  2. extractionthe mixture was extracted with ethylacetate
  3. washThe organic layer washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was purified by column chromatography on silica gel (eluent: dichloromethane/methanol=10/1-5/1)

Sources & evidence

ORD record
ord-584cb2296b4c4bafa4d01b1ec7659f67
Source dataset
uspto-grants-2011_11
Patent number
US08058245B2

Reaction notes

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