Ammonium Chloride → HCID 19849489, compound

HRID 1607820Notes

Reaction equation

HRID 1607820 reaction equation
C([Mg]Br)C.O1CCCCC1[O:11][CH2:12][C:13]#[C:14][CH2:15][C:16]#[CH:17].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+]>CCOCC.O1CCCC1>[O:23]([CH2:22][C:21]#[C:20][CH2:19][C:17]#[C:16][CH2:15][C:14]#[C:13][CH2:12][OH:11])[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 19849489HCID 19849489, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

3.99 ml (2.15 g, 0.016 mol) of a 4.05N solution of ethylmagnesium bromide in ether was added dropwise under argon to a solution of 2.879 (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 maintained at -20° C. After the addition was finished, the reactionmixture 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 was added. The reaction mixture was then stirredat room temperature for 3 hours, poured into 50 ml of saturated ammonium chloride solution and extracted with ether (3×50 ml). The combined extracts were dried over sodium sulfate and the solvent removed by evaporation in vacuo. The residue was purified by column chromatography on80 g of silica gel, using hexane:ether (90:10) as eluant thus obtaining thetetrahydropyranyl ether of 10-phenoxydeca-2,5,8-triyn-1-ol, as an oil. Thisproduct was stored in dry ice.

Workup

  1. additionAfter the addition
  2. stirringThe mixture was stirred for 20 additional minutes
  3. temperaturewarmed to room temperature
  4. waitstirredat room temperature for 3 hours
  5. extractionextracted with ether (3×50 ml)
  6. dry with materialThe combined extracts were dried over sodium sulfate
  7. customthe solvent removed by evaporation in vacuo
  8. customThe residue was purified by column chromatography on80 g of silica gel

Sources & evidence

ORD record
ord-407cbab170e54f4388cf5dc0e2ee2946
Source dataset
uspto-grants-1989_09
Patent number
US04867915

Reaction notes

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