Tetrahydrofuran → HCID 86745414, compound

HRID 1090843Notes

Reaction equation

HRID 1090843 reaction equation
[CH3:1][Mg]Cl.Br[CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][C:11]#[CH:12].[CH2:13]([Mg]Cl)[CH2:14]/[CH:15]=[CH:16]\[CH2:17]CCC.[O:23]1[CH2:27][CH2:26][CH2:25][CH2:24]1>>[CH3:1][CH:24]([OH:23])[C:25]#[C:26][CH2:27][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6]/[CH:5]=[CH:13]\[CH2:14][CH2:15][CH2:16][CH3:17]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 111061218-bromo-1-octyneHCID 178418332HCID 178418332, compoundHCID 178443578HCID 178443578, compound

Product 1

HCID 86745414HCID 86745414, compound

Conditions

Temperature
60 °C

Procedure

cis-13-Octadecen-3-yn-2-ol was synthesized in the following manner. Thus, a Grignard mixture containing 1.0 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise into 153 g (0.81 mole) of 8-bromo-1-octyne kept at 50° to 55° C. and the reaction mixture was agitated for 1 hour at 60° C. followed by the addition of 2 g of copper (I) iodide CuI. Thereafter, a second Grignard mixture containing 1.0 mole of cis-3-octenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture kept at 40° to 55° C. and the reaction mixture was agitated for 4 hours at 40° C.

Workup

  1. customkept at 50° to 55° C.
  2. additionwas added dropwise to the reaction mixture
  3. customkept at 40° to 55° C.
  4. stirringthe reaction mixture was agitated for 4 hours at 40° C.

Sources & evidence

ORD record
ord-1a15b7bd46fe443992b0cc19679b5121
Source dataset
uspto-grants-1992_01
Patent number
US05082961

Reaction notes

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