Potassium Carbonate → 197915-41-6

HRID 356553Notes

Reaction equation

HRID 356553 reaction equation
C([Si](C)(C)[O:6][CH2:7][CH2:8][O:9][C:10]1[CH:15]=[CH:14][C:13]([C:16]2([CH2:24][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[O:21][C:20](=[O:22])[CH:19]=[C:18]([OH:23])[CH2:17]2)=[CH:12][CH:11]=1)(C)(C)C.[C:34]([C:38]1[CH:43]=[C:42]([O:44][Si](C(C)(C)C)(C)C)[C:41]([CH3:52])=[CH:40][C:39]=1[S:53]S(C1C=CC(C)=CC=1)(=O)=O)([CH3:37])([CH3:36])[CH3:35].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[C:34]([C:38]1[CH:43]=[C:42]([OH:44])[C:41]([CH3:52])=[CH:40][C:39]=1[S:53][C:19]1[C:20](=[O:22])[O:21][C:16]([C:13]2[CH:12]=[CH:11][C:10]([O:9][CH2:8][CH2:7][OH:6])=[CH:15][CH:14]=2)([CH2:24][CH2:25][C:26]2[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=2)[CH2:17][C:18]=1[OH:23])([CH3:37])([CH3:36])[CH3:35]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 54265840HCID 54265840, compoundHCID 54682266HCID 54682266, compound

Product 1

HCID 54682296197915-41-6

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared as described in General Method 9 using 6-{4-[2-(tert-butyl-dimethyl-silanyloxy)-ethoxy]-phenyl }-4-hydroxy-6-phenethyl-5,6-dihydro-pyran-2-one (prepared in Example SS; 0.200 g, 0.43 mmol), toluene-4-thiosulfonic acid S-[2-tert-butyl-4-(tert-butyl-dimethyl-silanyloxy)-5-methyl-phenyl] ester prepared in Example JJJ (0.26 g, 0.56 mmol), K2CO3 (0.24 g, 1.7 mmol), and DMF (2.0 mL). After consumption of starting material, the mixture was diluted with MeOH and treated with 10 drops of concentrated HCl. The mixture was stirred for 20 minutes and then diluted with 15 mL of H2O and extracted with CH2Cl2. The organic layers were combined, dried (Na2SO4) and concentrated. The product was purified by column chromatography (CH2Cl2 to 4% MeOH in CH2Cl2) to provide a solid, m.p. 168°-170° C. (dec.). 1H NMR (DMSO-d6) δ 1.41 (s, 9 H), 1.63 (s, 3 H), 2.29-2.16 (m, 4 H), 3.32 (d, 1 H, partially obscured by H2O), 3.38 (d, 1 H, partially obscured by H2O), 3.98 (t, 2 H), 3.72 (br d, 2 H), 4.88 (br s, 1 H), 6.07 (s, 1 H), 6.71 (s, 1 H), 6.83 (d, 2 H), 7.09 (d, 2 H), 7.17-7.13 (m, 1 H), 7.26-7.22 (m, 2 H), 7.31 (d, 2 H), 8.91 (s, 1 H).

Workup

  1. customAfter consumption of starting material
  2. additionthe mixture was diluted with MeOH
  3. additiontreated with 10 drops of concentrated HCl
  4. additiondiluted with 15 mL of H2O
  5. extractionextracted with CH2Cl2
  6. dry with materialdried (Na2SO4)
  7. concentrationconcentrated
  8. customThe product was purified by column chromatography (CH2Cl2 to 4% MeOH in CH2Cl2)
  9. customto provide a solid, m.p. 168°-170° C. (dec.)

Sources & evidence

ORD record
ord-e751f1e622814d0195bfc7ad6e718680
Source dataset
uspto-grants-1998_11
Patent number
US05834506

Reaction notes

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