Hydrochloric Acid → 1-[4-(Tert-butoxycarbonyl)phenyl]-2-(4-n-propylphenyl)acetylene

HRID 493043Notes

Reaction equation

HRID 493043 reaction equation
C([C:5]1([CH:13]=[CH:12][C:11](Br)=[CH:10][CH2:9]1)[C:6]([O-:8])=[O:7])(C)(C)C.[CH2:15]([C:18]1[CH:23]=[CH:22][C:21]([C:24]#[CH:25])=[CH:20][CH:19]=1)[CH2:16][CH3:17].[CH2:26]([C:29]1[CH:34]=CC(Br)=C[CH:30]=1)CC.C[Si](C#C)(C)C.Cl>O>[C:29]([O:8][C:6]([C:5]1[CH:9]=[CH:10][C:11]([C:25]#[C:24][C:21]2[CH:20]=[CH:19][C:18]([CH2:15][CH2:16][CH3:17])=[CH:23][CH:22]=2)=[CH:12][CH:13]=1)=[O:7])([CH3:34])([CH3:30])[CH3:26]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 1363741-Bromo-4-propylbenzeneHCID 27751331-Ethynyl-4-propylbenzeneHCID 229258901-Tert-butyl-4-bromobenzoate

Product 1

HCID 229257481-[4-(Tert-butoxycarbonyl)phenyl]-2-(4-n-propylphenyl)acetylene

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction was conducted in the same manner as in the step (i) of the Example 31, except for using 1-tert-butyl-4-bromobenzoate synthesized in the step (i) of the Example 106 and 4-n-propylphenylacetylene synthesized in the step (ii) of the Example 31 instead of 1-n-propyl-4-bromobenzene and trimethylsilylacetylene, respectively. After completion of the reaction, the reaction mixture was poured into an iced water, and the resultant mixture was acidified by adding hydrochloric acid. The resultant solid was collected by filtration, washed with water, dried, and recrystallized from hexane to give 1-[4-(tert-butoxycarbonyl)phenyl]-2-(4-n-propylphenyl)acetylene.

Workup

  1. customAfter completion of the reaction
  2. filtrationThe resultant solid was collected by filtration
  3. washwashed with water
  4. customdried
  5. customrecrystallized from hexane

Sources & evidence

ORD record
ord-e7498c6b1f4643c78c2a73573bceed37
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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