Triethylamine → 4-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

HRID 23514Notes

Reaction equation

HRID 23514 reaction equation
[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:17])[CH3:16])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[CH:3]=1.C([SiH2][O:24][C:25](C)(C)[C:26]1[S:30][C:29]([CH:31]([CH3:33])[CH3:32])=[C:28]([S:34]S(C2C=CC(C)=CC=2)(=O)=O)[CH:27]=1)(C)(C)C.CCN(CC)CC.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O.C1COCC1.C(#N)C>[OH:1][C:2]1[CH2:7][C:6]([CH:15]([CH3:16])[CH3:17])([CH2:8][CH2:9][C:10]2[CH:14]=[CH:13][S:12][CH:11]=2)[O:5][C:4](=[O:18])[C:3]=1[S:34][C:28]1[CH:27]=[C:26]([CH2:25][OH:24])[S:30][C:29]=1[CH:31]([CH3:33])[CH3:32]

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 546770164-Hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-oneHCID 131723784HCID 131723784, compound

Product 1

HCID 546770324-Hydroxy-3-(5-hydroxymethyl-2-isopropyl-thiophen-3-ylsulfanyl)-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared according to General Method 16b using 4-hydroxy-6-isopropyl-6-(2-thiophen-3-yl-ethyl)-5,6-dihydro-pyran-2-one (Example E-20; 0.200 g, 0.75 mmol), toluene-4-thiosulfonic acid S-[5-(tert-butyl-dimethyl-silanyloxymethyl)-2-isopropyl-thiophen-3-yl]ester (Example BB-9; 0.377 g, 0.83 mmol), NEt3 (0.209 mL, 1.50 mmol), and acetonitrile (1.5 mL). As part of the purification, the silylether was cleaved by dissolving the crude coupled product in THF (50 mL) and then treated with a 1.0 M THF solution of tetrabutylammoniumflouride (1.5 mL, 1.5 mmol). After 30 minutes, the mixture was diluted with H2O and extracted with EtOAc. The organic layers were then combined, dried (MgSO4), and concentrated. The resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2) to provide the title compound, mp 52-54° C.

Workup

  1. customThe title compound was prepared
  2. customAs part of the purification
  3. dissolutionby dissolving the crude
  4. extractionextracted with EtOAc
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. washThe resulting residue was then submitted to column chromatography (eluting with 3% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-5ce9fcff9ef043ae914e9fd2b86977c5
Source dataset
uspto-grants-2005_02
Patent number
US06852711B2

Reaction notes

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