Hydrochloric Acid → HCID 178455743, compound

HRID 1982126Notes

Reaction equation

HRID 1982126 reaction equation
Br[C:2](Br)=[CH:3][C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:5]1.C([Li])CCC.O.Cl>O1CCCC1.CCCCCC>[C:3]([C@H:4]1[CH2:9][CH2:8][C@H:7]([CH2:10][CH2:11][CH2:12][CH3:13])[CH2:6][CH2:5]1)#[CH:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 178418339ButyllithiumHCID 178445604HCID 178445604, compound

Product 1

HCID 178455743HCID 178455743, compoundYield 92.4%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 162.1 g of trans-1-(2,2-dibromovinyl)-4-butylcyclohexane in 1.3 l of absolute tetrahydrofuran was cooled to -75° C. under nitrogen gasification and treated dropwise within 1 hour with 690 ml of a 1.6M solution of butyl lithium in hexane. The mixture was subsequently stirred at -70° C. for a further 2 hours, then poured into 1.5 l of water, neutralized with concentrated hydrochloric acid and extracted twice with 1 l of hexane each time. The combined organic phases were washed with 500 ml of water, dried over sodium sulphate and concentrated to dryness on a rotary evaporator. Distillation of the resulting light yellow crude product in a high vacuum gave in the main run 75.9 g (92.4%) of trans-1-ethynyl-4-butylcyclohexane as a colourless liquid; b.p. 41°-43° C./0.4 Torr.

Workup

  1. extractionextracted twice with 1 l of hexane each time
  2. washThe combined organic phases were washed with 500 ml of water
  3. dry with materialdried over sodium sulphate
  4. concentrationconcentrated to dryness on a rotary evaporator
  5. distillationDistillation of the resulting light yellow crude product in a high vacuum

Sources & evidence

ORD record
ord-2cb5bef7f2a54ad089d40700a7dbc531
Source dataset
uspto-grants-1986_06
Patent number
US04595521

Reaction notes

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