Potassium Carbonate → HCID 45079102, compound

HRID 382844Notes

Reaction equation

HRID 382844 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 2h. It was treated with NH4Cl solution, evaporated MeOH and the residue extracted with EtOAc (3×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,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×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-9a7d14648b1047008f73c5a3d5f28a73
Source dataset
uspto-grants-2001_10
Patent number
US06310221B1

Reaction notes

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