Tetrahydrofuran → HCID 11821510, compound

HRID 1090844Notes

Reaction equation

HRID 1090844 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][C:8]#[CH:9].C[Mg]Cl.[CH2:13]([Mg]Cl)[CH2:14][CH2:15]/[CH:16]=[CH:17]\[CH2:18]CCC.[O:24]1[CH2:28][CH2:27][CH2:26][CH2:25]1>>[CH2:25]([OH:24])[C:26]#[C:27][CH2:28][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]/[CH:13]=[CH:14]\[CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 111061218-bromo-1-octyneHCID 178418332HCID 178418332, compoundHCID 178443477HCID 178443477, compound

Product 1

HCID 11821510HCID 11821510, compound

Procedure

cis-13-Octadecen-2-yn-1-ol was synthesized in the following manner. Thus, 153 g (0.81 mole) of 8-bromo-1-octyne were added dropwise at 50° to 55° C. to 1 mole of methyl magnesium chloride dissolved in 300 ml of tetrahydrofuran and the mixture was agitated for 1 hour followed by the addition of 2 g of dilithium tetrachlorocuprate Li2CuCl4. Thereafter, a solution of 1 mole of cis-4-nonenyl magnesium chloride dissolved in 300 ml of tetrahydrofuran was added dropwise to the reaction mixture at 40° to 55° C. and the mixture was agitated for 4 hours at 48° C.

Workup

  1. additionwas added dropwise to the reaction mixture at 40° to 55° C.
  2. stirringthe mixture was agitated for 4 hours at 48° C.

Sources & evidence

ORD record
ord-237daaa6ef544910abb5e618bd373d08
Source dataset
uspto-grants-1992_01
Patent number
US05082961

Reaction notes

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