Potassium Carbonate → HCID 12066282, compound

HRID 382842Notes

Reaction equation

HRID 382842 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 3h. 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,5S)-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): δ 1.9-2.38 (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): δ 26.6, 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-e2312d5ba3c84a3c9fa915a191d2cdfe
Source dataset
uspto-grants-2001_10
Patent number
US06310221B1

Reaction notes

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