Hydrochloric Acid → HCID 59408344, compound

HRID 2389214Notes

Reaction equation

HRID 2389214 reaction equation
[Li]CCCC.Br[C:7](Br)=[CH:8][CH:9]1[CH2:14][CH2:13][CH:12]([CH:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH3:29])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:11][CH2:10]1.O.Cl>C1COCC1>[C:8]([CH:9]1[CH2:10][CH2:11][CH:12]([CH:15]2[CH2:20][CH2:19][CH:18]([C:21]3[CH:26]=[CH:25][C:24]([CH2:27][CH2:28][CH3:29])=[CH:23][CH:22]=3)[CH2:17][CH2:16]2)[CH2:13][CH2:14]1)#[CH:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 59408358HCID 59408358, compoundHCID 178418339Butyllithium

Product 1

HCID 59408344HCID 59408344, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-20 °C

Procedure

23.7 ml (38.0 mmol) of n-BuLi are added to 7.70 g (16.4 mmol) of 4-(2,2-dibromovinyl)-4′-(4-propylphenyl)bicyclohexyl in 40 ml of THF at −75° C. When the addition is complete, the mixture is stirred at this temperature for 2 h and subsequently warmed to −20° C. Water and dil. hydrochloric acid are added, and the batch is extracted a number of times with MTBE. The combined organic phases are washed with water and sat. sodium chloride solution and dried using sodium sulfate. The solution is concentrated to completion, and the residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=95:5). 4-Ethynyl-4′-(4-propylphenyl)bicyclohexyl is obtained as a colourless solid.

Workup

  1. additionWhen the addition
  2. extractionthe batch is extracted a number of times with MTBE
  3. washThe combined organic phases are washed with water and sat. sodium chloride solution
  4. customdried
  5. concentrationThe solution is concentrated to completion
  6. customthe residue is purified by column chromatography (SiO2, n-heptane:1-chlorobutane=95:5)

Sources & evidence

ORD record
ord-bd2f1dd387194787b3f530d14170493f
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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