Potassium Carbonate → HCID 12066282, compound

HRID 1264185Notes

Reaction equation

HRID 1264185 reaction equation
C(O[C@@H:5]([CH2:8][CH2:9][C@H:10]([OH:23])[CH2:11][O:12]S(C1C=CC(C)=CC=1)(=O)=O)[C:6]#[CH:7])(=O)C.C([O-])([O-])=O.[K+].[K+].[NH4+].[Cl-]>CO>[C:6]([C@H:5]1[O:23][C@H:10]([CH2:11][OH:12])[CH2:9][CH2:8]1)#[CH:7]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 25517Ammonium ChlorideHCID 12066280HCID 12066280, compound

Product 1

HCID 12066282HCID 12066282, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of (3S,6S)-3-acetoxy-6-hydroxy-7-p-toluene sulfonyloxy-hept-1-yne 15 (3.67 g, 10.79 mmol) in MeOH (50 mL) at room temperature, was treated with K2CO3 (3.2 g, 23.7 mmol) and stirred for 3 h. It was further treated with NH4Cl solution, evaporated MeOH and residue extracted with EtOAc (3×50 mL). Organic layer was washed with water (2×25 mL), brine (25 mL), dried (Na2SO4), and evaporated. The residue obtained was purified by column chromatography (Si-gel, 20% EtOAc-hexane) to afford (2S,55)-5-ethynyl-2-(hydroxymethyl)-tetrahydrofuran 16 (1.35 g) in 90% yield as a colorless liquid. [α]D−15.07 (c 1.26, CHCl3); 1HNMR (CDCl3, 200 MHz): δ1.9-2.38 (m, 4H, H-3,4), 2.45 (d, 1H, J 2.1 Hz, H-7), 3.55 (dd, 1H, J 6.3, 12.75 Hz, H-1), 3.72 (dd, 1H, J 3.8, 12.75 Hz, H-1a), 4.0-4.18 (m, 1H, H-2), 4.55-4.65 (m, 1H, H-5); 13CNMR (CDCl3, 50 MHz): δ26.6, 29.64, 64.62, 68.33, 73.11, 80.7, 83.92.

Workup

  1. customevaporated MeOH and residue
  2. extractionextracted with EtOAc (3×50 mL)
  3. washOrganic layer was washed with water (2×25 mL), brine (25 mL)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by column chromatography (Si-gel, 20% EtOAc-hexane)

Sources & evidence

ORD record
ord-d1814bfab85a4a6d890a0a1a1d314a50
Source dataset
uspto-grants-2003_04
Patent number
US06541647B2

Reaction notes

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