Potassium Carbonate → HCID 23507944, compound

HRID 1654340Notes

Reaction equation

HRID 1654340 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, ethynyl H), 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-330fbee1a4ba4b64b1b1f10e44fb446e
Source dataset
uspto-grants-1995_04
Patent number
US05405851

Reaction notes

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