Ammonium Chloride → 10-Phenoxydeca-2,5,8-triyn-1-ol tetrahydropyranyl ether

HRID 652119Notes

Reaction equation

HRID 652119 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][CH2:11][C:12]#[CH:13].C([Mg]Br)C.I[CH2:19][C:20]#[C:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[Cl-].[NH4+]>O1CCCC1.CCOCC>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][C:9]#[C:10][CH2:11][C:12]#[C:13][CH2:19][C:20]#[C:21][CH2:22][O:23][C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 5340252-(2,5-Hexadiynyloxy)tetrahydro-2H-pyranHCID 198494611-Iodo-4-phenoxybut-2-yneHCID 178418443HCID 178418443, compound

Product 1

HCID 2019937910-Phenoxydeca-2,5,8-triyn-1-ol tetrahydropyranyl ether

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

To a cold (-20° C.) solution of 2.879 g (0.0161 mol) of hexa-2,5-diyn-1-ol tetrahydropyranyl ether [D. Van der Steen et al, Recueil 82, 1015 (1963)] in 30 ml of tetrahydrofuran, there were added dropwise, under argon atmosphere, 4.0 ml (2.15 g, 0.016 mol) of a 4.05N solution of ethylmagnesium bromide in ether, maintaining the temperature at -20° C. After the addition was finished, the reaction mixture was stirred for 2 hours further at -20° C. Then, 52.8 mg (0.53 mmol) of cuprous chloride was added. The mixture was stirred for 20 additional minutes, warmed to room temperature and 2.2 g (0.008 mol) of 1-iodo-4-phenoxybut-2-yne were added. The reaction mixture was then stirred at room temperature for 3 hours, poured into 50 ml of saturated ammonium chloride solution and extracted with ether. The combined extracts were dried and evaporated in vacuo. The residue was purified by column chromatography on 80 g of silica gel, using hexane-ether (90:10) as eluant, thus obtaining 10-phenoxydeca-2,5,8-triyn-1-ol tetrahydropyranyl ether, as an oil.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred for 20 additional minutes
  3. temperaturewarmed to room temperature
  4. stirringThe reaction mixture was then stirred at room temperature for 3 hours
  5. extractionextracted with ether
  6. customThe combined extracts were dried
  7. customevaporated in vacuo
  8. customThe residue was purified by column chromatography on 80 g of silica gel

Sources & evidence

ORD record
ord-cd34bbb5d8aa47b58a2836a7daeeb6ef
Source dataset
uspto-grants-1987_06
Patent number
US04670465

Reaction notes

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