Methyl 4-trimethylsilylethynylbenzoate → HCID 19068299, compound

HRID 1957690Notes

Reaction equation

HRID 1957690 reaction equation
[C:1]12([C:11]3[CH:12]=[C:13]([CH:17]=[CH:18][C:19]=3[O:20][CH3:21])[C:14](Cl)=[O:15])[CH2:10][CH:5]3[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]3)[CH2:2]1)[CH2:8]2.C[Si]([C:26]#[C:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1)(C)C.[Al+3].[Cl-].[Cl-].[Cl-]>ClCCl>[O:15]=[C:14]([C:13]1[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:11]([C:1]23[CH2:10][CH:5]4[CH2:6][CH:7]([CH2:9][CH:3]([CH2:4]4)[CH2:2]2)[CH2:8]3)[CH:12]=1)[C:26]#[C:27][C:28]1[CH:37]=[CH:36][C:31]([C:32]([O:34][CH3:35])=[O:33])=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 640161Methyl 4-trimethylsilylethynylbenzoateHCID 6451240Aluminum(III) ChlorideHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chloride

Product 1

HCID 19068299HCID 19068299, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

3 g (10 mmol) of 3-(1-adamantyl)-4-methoxybenzoyl chloride, 2.3 g (10 mmol) of the above compound (a) and 100 ml of dichloromethane were introduced into a round-bottomed flask. 4.7 g (35 mmol) of AlCl3 were added portionwise, at 0° C., and the mixture was stirred at room temperature for 8 hours. The reaction medium was poured into ice and extracted with dichloromethane. The organic phase was separated out after settling had taken place, dried over magnesium sulfate and evaporated. The residue obtained was purified by chromatography on a column of silica, eluted with a mixture of dichloromethane and hexane (80/20). 970 mg (23%) of the expected compound, having a melting point of 156°-8° C., were recovered.

Workup

  1. additionThe reaction medium was poured into ice
  2. extractionextracted with dichloromethane
  3. customThe organic phase was separated out
  4. dry with materialdried over magnesium sulfate
  5. customevaporated
  6. customThe residue obtained
  7. customwas purified by chromatography on a column of silica
  8. washeluted with a mixture of dichloromethane and hexane (80/20)
  9. customwere recovered

Sources & evidence

ORD record
ord-a7fb857ca36d42c991417cba3a610e67
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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