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Hydrochloric Acid → 2-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene

HRID 1873389
Notes
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Reaction equation

HRID 1873389 reaction equation
[CH3:1][C:2](C)([O-])C.[K+].[CH2:7]([CH:10]1[CH2:15][CH2:14][CH:13]([C:16]2[CH:21]=[CH:20][C:19]([C:22]3[Se:26][C:25]([CH:27]=O)=[CH:24][CH:23]=3)=[CH:18][CH:17]=2)[CH2:12][CH2:11]1)[CH2:8][CH3:9].Cl>[Br-].C([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)C.C1COCC1.CC(OC)(C)C.[Cl-].[NH4+]>[CH:27]([C:25]1[Se:26][C:22]([C:19]2[CH:20]=[CH:21][C:16]([CH:13]3[CH2:14][CH2:15][CH:10]([CH2:7][CH2:8][CH3:9])[CH2:11][CH2:12]3)=[CH:17][CH:18]=2)=[CH:23][CH:24]=1)=[CH:1][CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 3

HCID 313Hydrochloric AcidHCID 23665647Potassium tert-butoxideHCID 594562815-[4-(4-Propylcyclohexyl)phenyl]selenophene-2-carbaldehyde

Product 1

HCID 722902572-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene

Reagents, catalysts & solvents 4

HCID 73727Phosphonium, ethyltriphenyl-, bromide (1:1)Catalyst
HCID 8028TetrahydrofuranSolvent2×
HCID 15413tert-Butyl methyl etherSolvent
HCID 25517Ammonium ChlorideSolvent

Procedure

1.80 g (4.85 mmol) of ethyltriphenylphosphonium bromide are initially introduced in 8 ml of THF at 0° C., and 533 mg (4.75 mmol) of potassium tert-butoxide are added. After 1.5 h at RT, a solution of 1.16 g (3.23 mmol) of 5-[4-(4-propylcyclohexyl)phenyl]selenophene-2-carbaldehyde in 7 ml of THF is added, and the batch is stirred for 2.5 h. The mixture is diluted with MTBE, and sat. ammonium chloride soln. and 2 N hydrochloric acid are added. The organic phase is separated off, and the aqueous phase is extracted with MTBE. The combined organic phases are washed with sat. sodium chloride soln. and dried using sodium sulfate. The solution is concentrated to dryness, and the residue is purified by column chromatography (SiO2, n-heptane→n-heptane:EtOAc=20:1). 2-(Propenyl)-5-[4-(4-propylcyclohexyl)phenyl]selenophene is obtained as an E/Z isomer mixture.

Workup

  1. customThe organic phase is separated off
  2. extractionthe aqueous phase is extracted with MTBE
  3. washThe combined organic phases are washed with sat. sodium chloride soln
  4. customand dried
  5. concentrationThe solution is concentrated to dryness
  6. customthe residue is purified by column chromatography (SiO2, n-heptane→n-heptane:EtOAc=20:1)

Sources & evidence

ORD record
ord-d5bb2c20a2c24e3886367c461b81c583
Source dataset
uspto-grants-2012_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08304036B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes