Water → HCID 59408352, compound

HRID 2389207Notes

Reaction equation

HRID 2389207 reaction equation
C[Si](C)(C)[C:3]#[C:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:7][CH:6]=1.C([O-])([O-])=O.[K+].[K+].O>CO.CC(OC)(C)C.Cl>[C:4]([C:5]1[CH:6]=[CH:7][C:8]([CH:11]2[CH2:16][CH2:15][CH:14]([CH:17]3[CH2:22][CH2:21][CH:20]([CH2:23][CH2:24][CH3:25])[CH2:19][CH2:18]3)[CH2:13][CH2:12]2)=[CH:9][CH:10]=1)#[CH:3]

Participants

7

Reactant 3

HCID 962WaterHCID 11430Potassium CarbonateHCID 59408341HCID 59408341, compound

Product 1

HCID 59408352HCID 59408352, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

20.0 g (52.5 mmol) of trimethyl-[4-(4′-propylbicyclohexyl-4-yl)phenylethynyl]silane are stirred for 48 h together with 8.71 g (63.0 mmol) of K2CO3 and 1.5 ml of water in 250 ml of methanol. The mixture is diluted with MTBE and neutralised using dil. hydrochloric acid. The aqueous phase is extracted with MTBE, and the combined organic phases are washed with water and sat. sodium chloride solution. The solution is dried using sodium sulfate and concentrated to completion. The crude product is recrystallised from n-heptane. 4′-(4-Ethynylphenyl)-4-propylbicyclohexyl is obtained as a colourless solid having an m.p. of 71° C.

Workup

  1. extractionThe aqueous phase is extracted with MTBE
  2. washthe combined organic phases are washed with water and sat. sodium chloride solution
  3. customThe solution is dried
  4. concentrationconcentrated to completion
  5. customThe crude product is recrystallised from n-heptane

Sources & evidence

ORD record
ord-8130337dc1274dbc98f01bf2d33b5f12
Source dataset
uspto-grants-2012_09
Patent number
US08273264B2

Reaction notes

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