Hydrochloric Acid → HCID 22925747, compound

HRID 493032Notes

Reaction equation

HRID 493032 reaction equation
[CH2:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[CH:11])=[CH:6][CH:5]=1)[CH2:2][CH3:3].[C:12]([O:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=1)=[O:18])([CH3:15])([CH3:14])[CH3:13].C(C1C=CC(Br)=CC=1)CC.C[Si](C#C)(C)C.Cl>O>[C:12]([O:16][C:17]([O:19][C:20]1[CH:25]=[CH:24][C:23]([C:11]#[C:10][C:7]2[CH:6]=[CH:5][C:4]([CH2:1][CH2:2][CH3:3])=[CH:9][CH:8]=2)=[CH:22][CH:21]=1)=[O:18])([CH3:15])([CH3:13])[CH3:14]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 1363741-Bromo-4-propylbenzeneHCID 27751331-Ethynyl-4-propylbenzeneHCID 22345880HCID 22345880, compound

Product 1

HCID 22925747HCID 22925747, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The reaction was carried out in the same manner as in the step (i), except for using 4-n-propylphenylacetylene synthesized in the step (ii) and 1-(tert-butoxycarbonyloxy)-4-bromobenzene synthesized in the Example 4 instead of 1-n-propyl-4-bromobenzene and trimethylsilylacetylene, respectively. After completion of the reaction, the reaction solution was poured into an iced water, and the resultant solution was acidified by adding hydrochloric acid. After the resultant solid was collected by filtration, the collected solid was washed with water, dried, and recrystallized successively from hexane and ethanol to provide 4.1 g (12.1 mmol) of 1-[4-(tert-butoxycarbonyloxy)phenyl]-2-(4-n-propylphenyl)acetylene.

Workup

  1. customAfter completion of the reaction
  2. filtrationAfter the resultant solid was collected by filtration
  3. washthe collected solid was washed with water
  4. customdried
  5. customrecrystallized successively from hexane and ethanol

Sources & evidence

ORD record
ord-7c7d30d5d4d34fc094fd51e2321991ca
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

Loading…