Tetrahydrofuran → Allyl 4-[3-(1-adamantyl)-4-methoxyethoxymethoxybenzamido]benzoate

HRID 1957695Notes

Reaction equation

HRID 1957695 reaction equation
[NH2:1][C:2]1[CH:13]=[CH:12][C:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])=[CH:4][CH:3]=1.C(N(CC)CC)C.C1COCC1.[C:26]12([C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=3[O:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH3:51])[C:39](Cl)=[O:40])[CH2:35][CH:30]3[CH2:31][CH:32]([CH2:34][CH:28]([CH2:29]3)[CH2:27]1)[CH2:33]2>O>[C:26]12([C:36]3[CH:37]=[C:38]([CH:42]=[CH:43][C:44]=3[O:45][CH2:46][O:47][CH2:48][CH2:49][O:50][CH3:51])[C:39]([NH:1][C:2]3[CH:3]=[CH:4][C:5]([C:6]([O:8][CH2:9][CH:10]=[CH2:11])=[O:7])=[CH:12][CH:13]=3)=[O:40])[CH2:27][CH:28]3[CH2:29][CH:30]([CH2:31][CH:32]([CH2:34]3)[CH2:33]1)[CH2:35]2

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13075143Prop-2-en-1-yl 4-aminobenzoateHCID 572331023-(1-Adamantyl)-4-methoxyethoxymethoxybenzoyl chloride

Product 1

HCID 67663874Allyl 4-[3-(1-adamantyl)-4-methoxyethoxymethoxybenzamido]benzoate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

700 mg (3.95 mmol) of allyl 4-aminobenzoate, 1 ml (4.3 mmol) of triethylamine and 50 ml of THF were introduced into a round-bottomed flask. A solution of 1.5 g (3.96 mmol) of 3-(1-adamantyl)-4-methoxyethoxymethoxybenzoyl chloride was added dropwise and the mixture was stirred at room temperature for 4 hours. The reaction medium was poured into water and extracted with ethyl ether. 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 dichloromethane. 1.7 g (83%) of the expected allylic ester was recovered in the form of an oil.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase was separated out
  3. dry with materialdried over magnesium sulfate
  4. customevaporated
  5. customThe residue obtained
  6. customwas purified by chromatography on a column of silica
  7. washeluted with dichloromethane
  8. custom1.7 g (83%) of the expected allylic ester was recovered in the form of an oil

Sources & evidence

ORD record
ord-b46855fa87a44f10b58563b1917e71b5
Source dataset
uspto-grants-1998_07
Patent number
US05786379

Reaction notes

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