Potassium Carbonate → HCID 45079102, compound

HRID 413580Notes

Reaction equation

HRID 413580 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 22959681HCID 22959681, compound

Product 1

HCID 45079102HCID 45079102, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of (3R,6R)-3-acetoxy-6-hydroxy-7-p-toluene sulfonyloxy-hept-1-yne 31 (0.6 g, 1.76 mmol) in MeOH (10 mL) at room temperature, K2CO3 (0.536 g, 3.88 mmol) was added and the mixture was stirred for 2 h. 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 columnn chromatography (Si-gel, 20% EtOAc-hexane) to furnish (2R,5R)-5-ethynyl-2-(hydroxymethyl)-tetrahydrofuran 32 (0.22 g) in 99% yield as a colorless liquid. [α]D+20.0 (c 1.0, CHCl3); 1HNMR (CDCl3, 200 MHz): δ 1.89-2.38 (m, 4H, H-3,4), 2.4 (br.s, 1H, OH), 2.46 (d, 1H, J 2.2 Hz, H-7), 3.55 (dd, 1H, J 4.5, 11.25 Hz, H-1), 3.72 (dd, 1H, J 4.0, 11.25 Hz, H-1a), 4.0-4.15 (m, 1H, H-2), 4.52-4.66 (m, 1H, H-5); 13CNMR (CDCl3, 50 MHz): δ 26.6, 29.6, 33.6, 64.6, 68.3, 73.0, 80.7; EIMS m/z (relative intensity): 125 (M+−1, 8), 95 (74.6), 67 (100), 53 (40), 41 (80); HRMS: Calculated for C7H9O2 (M-1): 125.060255; Observed: 125.060322.

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 columnn chromatography (Si-gel, 20% EtOAc-hexane)

Sources & evidence

ORD record
ord-fdf8f094463843818ae74efa11d0e70c
Source dataset
uspto-grants-2003_05
Patent number
US06566538B1

Reaction notes

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