Potassium Carbonate → 3-(3-tert-Butyl-benzo[b]thiophen-2-yl-sulfanyl)-4-hydroxy-6-[2-(2-hydroxymethyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

HRID 23513Notes

Reaction equation

HRID 23513 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][OH:20])([CH:8]([CH3:10])[CH3:9])[O:5][C:4](=[O:21])[CH:3]=1.[C:22]([C:26]1[C:27]2[CH:45]=[CH:44][CH:43]=[CH:42][C:28]=2[S:29][C:30]=1[S:31]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:25])([CH3:24])[CH3:23].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[C:22]([C:26]1[C:27]2[CH:45]=[CH:44][CH:43]=[CH:42][C:28]=2[S:29][C:30]=1[S:31][C:3]1[C:4](=[O:21])[O:5][C:6]([CH2:11][CH2:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[CH2:19][OH:20])([CH:8]([CH3:9])[CH3:10])[CH2:7][C:2]=1[OH:1])([CH3:25])([CH3:23])[CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12073546toluene-4-thiosulfonic acid S-(3-tert-butyl-benzo[b]thiophen-2-yl)esterHCID 697346654-Hydroxy-6-[2-(2-hydroxymethyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Product 1

HCID 546770103-(3-tert-Butyl-benzo[b]thiophen-2-yl-sulfanyl)-4-hydroxy-6-[2-(2-hydroxymethyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to General Method 16a using 4-hydroxy-6-[2-(2-hydroxymethyl-phenyl)-ethyl]-6-isopropyl-5,6-dihydro-pyran-2-one (Example E-34; 0.20 g, 0.73 mmol), toluene-4-thiosulfonic acid S-(3-tert-butyl-benzo[b]thiophen-2-yl)ester (Example BB-8; 0.302 g, 0.803 mmol), potassium carbonate (0.11 g, 0.80 mmol), and DMF (2.0 mL). The product was purified via column chromatography (eluting with EtOAc) to the title compound, mp 92-94° C.

Workup

  1. customThe product was purified via column chromatography (eluting with EtOAc) to the title compound, mp 92-94° C.

Sources & evidence

ORD record
ord-a19f65f869be445a99fc57e64952d905
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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