Water → Allyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy-]2-fluorobenzoate

HRID 1589966Notes

Reaction equation

HRID 1589966 reaction equation
[F:1][C:2]1[CH:13]=[C:12]([OH:14])[CH:11]=[CH:10][C:3]=1[C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5].C(N(CC)CC)C.[C:22]12([C:32]3[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=3[O:41][CH3:42])[C:35](Cl)=[O:36])[CH2:31][CH:26]3[CH2:27][CH:28]([CH2:30][CH:24]([CH2:25]3)[CH2:23]1)[CH2:29]2.O>C1COCC1>[C:22]12([C:32]3[CH:33]=[C:34]([CH:38]=[CH:39][C:40]=3[O:41][CH3:42])[C:35]([O:14][C:12]3[CH:11]=[CH:10][C:3]([C:4]([O:6][CH2:7][CH:8]=[CH2:9])=[O:5])=[C:2]([F:1])[CH:13]=3)=[O:36])[CH2:23][CH:24]3[CH2:30][CH:28]([CH2:27][CH:26]([CH2:25]3)[CH2:31]1)[CH2:29]2

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 108044973-(1-Adamantyl)-4-methoxybenzoyl chlorideHCID 14852522Allyl 2-fluoro-4-hydroxybenzoate

Product 1

HCID 14852489Allyl 4-[3-(1-adamantyl)-4-methoxybenzoyloxy-]2-fluorobenzoateYield 78.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 1.96 g (10 mmoles) of allyl 2-fluoro-4-hydroxybenzoate, 1.53 ml (11 mmoles) of triethylamine and 25 ml of THF, there is slowly added a solution of 3 g (10 mmoles) of 3-(1-adamantyl)-4-methoxybenzoyl chloride in 50 ml of THF. The reaction medium is stirred at ambient temperature for 12 hours and then poured into water and extracted with ethyl ether. The organic phase is decanted, washed with water, dried on magnesium sulfate and evaporated. The resulting residue is purified by chromatography on a silica column, eluted by a 50:50 mixture of dichloromethane and hexane. After evaporation of the solvents, 3.63 g (78% yield) of the expected ester having a melting point of 102°-104° C.

Workup

  1. extractionextracted with ethyl ether
  2. customThe organic phase is decanted
  3. washwashed with water
  4. customdried on magnesium sulfate
  5. customevaporated
  6. customThe resulting residue is purified by chromatography on a silica column
  7. washeluted by a 50:50 mixture of dichloromethane and hexane

Sources & evidence

ORD record
ord-ccc4f72bafcc43a7801dc33c9d15c9b7
Source dataset
uspto-grants-1993_04
Patent number
US05200550

Reaction notes

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