Tetrahydrofuran → HCID 10955105, compound

HRID 2308395Notes

Reaction equation

HRID 2308395 reaction equation
C1COCC1.Br[C:7](Br)=[CH:8][CH2:9][CH2:10]/[CH:11]=[C:12](\[CH3:22])/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21].[Li]CCCC>CCCCCC>[CH3:22]/[C:12](/[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH3:21])=[CH:11]\[CH2:10][CH2:9][C:8]#[CH:7]

Participants

5

Reactant 3

HCID 8028TetrahydrofuranHCID 22602342HCID 22602342, compoundHCID 178418339Butyllithium

Product 1

HCID 10955105HCID 10955105, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a stirred and cooled THF (400 ml) solution of the (E)-1,1-dibromo-6-methyl-1,5-pentadecadiene (6) (37.0 g, 97.6 mmols), an n-hexane solution of n-BuLi (1.5 M, 150 ml, 225 mmols) was added dropwise at −70° C. under an Ar gas. The mixture was stirred for 1 hour at −70° C. and for 1.5 hours at room temperature. Then, the reaction mixture was poured into 1.5 liters of ice water, and extracted with n-hexane. The hexane solution was washed with water, dried with sodium sulfate, and concentrated in a vacuum. The residue was subjected to silica gel column chromatography, and eluted with n-hexane to obtain 18.9 g (88.0%) of (E)-6-methyl-5-pentadecen-1-yne (7) as oily matter.

Workup

  1. stirringThe mixture was stirred for 1 hour at −70° C. and for 1.5 hours at room temperature
  2. extractionextracted with n-hexane
  3. washThe hexane solution was washed with water
  4. dry with materialdried with sodium sulfate
  5. concentrationconcentrated in a vacuum
  6. washeluted with n-hexane

Sources & evidence

ORD record
ord-e295c513270549ddb3a7cda3ef01e585
Source dataset
uspto-grants-2004_12
Patent number
US06835846B2

Reaction notes

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