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

HRID 493042Notes

Reaction equation

HRID 493042 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]([O:18][C:19]1[CH:24]=[CH:23][C:22]([C:25]#[CH:26])=[CH:21][CH:20]=1)[CH2:16][CH3:17].[CH2:27]([C:30]1[CH:35]=CC(Br)=C[CH:31]=1)CC.C[Si](C#C)(C)C.Cl>O>[C:30]([O:8][C:6]([C:5]1[CH:9]=[CH:10][C:11]([C:26]#[C:25][C:22]2[CH:21]=[CH:20][C:19]([O:18][CH2:15][CH2:16][CH3:17])=[CH:24][CH:23]=2)=[CH:12][CH:13]=1)=[O:7])([CH3:35])([CH3:31])[CH3:27]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 66111TrimethylsilylacetyleneHCID 1363741-Bromo-4-propylbenzeneHCID 27751231-Ethynyl-4-propoxybenzeneHCID 229258901-Tert-butyl-4-bromobenzoate

Product 1

HCID 229258451-[4-(Tert-butoxycarbonyl)phenyl]-2-(4-n-propyloxyphenyl)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) and 4-n-propyloxyphenylacetylene synthesized in the step (iii) of the Example 32 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-propyloxyphenyl)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-41726123643a468e84f1e45cb2379082
Source dataset
uspto-grants-2009_05
Patent number
US07534547B2

Reaction notes

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