Potassium Carbonate → HCID 45079101, compound

HRID 382845Notes

Reaction equation

HRID 382845 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 22986700HCID 22986700, compound

Product 1

HCID 45079101HCID 45079101, compoundYield 120.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3S,6R)-3-acetoxy-6-hydroxy-7-p-toluene sulfonyloxy-hept-1-yne 48 (0.9 g, 2.64 mmol) in MeOH (15 mL) at room temperature, K2CO3 (0.805 g, 5.83 mmol) was added and the mixture was stirred for 2h. It was treated with NH4Cl solution, evaporated MeOH and the residue extracted with EtOAc (3×20 mL). Organic layer was washed with water (10 mL), brine (10 mL), dried (Na2SO4) evaporated. The residue obtained was purified by column chromatography (Si-gel, 20% EtOAc-hexane) to furnish (2R,5S)-5-ethynyl-2-(hydroxymethyl)-tetrahydrofuran 49 (0.4 g) in 95% yield as a colorless liquid. [α]D −10.5 (c 1.0, CHCl3); 1HNMR (CDCl3, 200 MHz): δ 1.50-2.3 (m, 4H, H-3,4), 2.4 (br.s, 1H, OH), 2.42 (d, 1H, J 2.2 Hz, H-7), 3.5 (dd, 1H, J 4.5, 11.3 Hz, H-1), 3.75 (dd, 1H, J 3.3, 11.35 Hz, H-1a), 4.16-4.34 (m, 1H, H-2), 4.6-4.74 (m, 1H, H-5)

Workup

  1. customevaporated MeOH
  2. extractionthe residue extracted with EtOAc (3×20 mL)
  3. washOrganic layer was washed with water (10 mL), brine (10 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-96050e85dee74da3b4c84ec588944c7e
Source dataset
uspto-grants-2001_10
Patent number
US06310221B1

Reaction notes

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