Potassium Carbonate → HCID 23507944, compound

HRID 1883987Notes

Reaction equation

HRID 1883987 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][C:11]3([O:18][CH2:17][CH2:16][O:15]3)[CH2:12]2)=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+]>CO>[C:4]([C:5]1[CH:14]=[C:13]2[C:8]([CH2:9][CH2:10][C:11]3([O:15][CH2:16][CH2:17][O:18]3)[CH2:12]2)=[CH:7][CH:6]=1)#[CH:3]

Participants

4

Reactant 2

HCID 11430Potassium CarbonateHCID 23507984HCID 23507984, compound

Product 1

HCID 23507944HCID 23507944, compoundYield 79%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A solution of 3′,4′dihydro-7′[2-(trimethylsilyl)ethynyl]spiro[1,3-dioxolane-2,2′(1′H)-naphthalene] (1.45 g, 5.02 mmol) and suspended K2CO3 (0.50 g) in methanol (20 ml) was stirred at room temperature for 30 minutes. The solution was then filtered and concentrated in vacuo. The residue was absorbed onto silica gel (2 g) and purified by chromatography on silica gel (11 g) eluting with diethyl ether:hexane (1:9) to give 7′-ethynyl-3′,4′-dihydrospiro[1,3-dioxolane-2,2′(1′H)-naphthalene] as a solid (0.85 g). 1H NMR (CDCl3, 200 MHz) δ: 1.94 (t, J=7 Hz, 2H, CH2), 2.95 (s, 2H, CH2), 2.98 (t, J=7 Hz, 2H, CH2), 3.01 (s, 1H, ethynylH), 4.02 (s, 4H, OCH2CH2O), 7.07 (d, J=8 Hz, 1H, Ar), 7.19 (s, 1H, Ar), 7.24 (d, J=8 Hz, 1H, Ar).

Workup

  1. filtrationThe solution was then filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue was absorbed onto silica gel (2 g)
  4. custompurified by chromatography on silica gel (11 g)
  5. washeluting with diethyl ether:hexane (1:9)

Sources & evidence

ORD record
ord-334a5b8269fd4a7c858119858e16ef3d
Source dataset
uspto-grants-2004_07
Patent number
US06762188B1

Reaction notes

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