Potassium Carbonate → Methyl 2-hydroxy-4-[7-(1-adamantyl)-6-benzyloxy-2-naphthyl]benzoate

HRID 618481Notes

Reaction equation

HRID 618481 reaction equation
[OH:1][C:2]1[CH:11]=[C:10](I)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].[C:13]12([C:23]3[CH:32]=[C:31]4[C:26]([CH:27]=[CH:28][C:29](B(O)O)=[CH:30]4)=[CH:25][C:24]=3[O:36][CH2:37][C:38]3[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=3)[CH2:22][CH:17]3[CH2:18][CH:19]([CH2:21][CH:15]([CH2:16]3)[CH2:14]1)[CH2:20]2.C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[OH:1][C:2]1[CH:11]=[C:10]([C:29]2[CH:28]=[CH:27][C:26]3[C:31](=[CH:32][C:23]([C:13]45[CH2:14][CH:15]6[CH2:21][CH:19]([CH2:18][CH:17]([CH2:16]6)[CH2:22]4)[CH2:20]5)=[C:24]([O:36][CH2:37][C:38]4[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:25]=3)[CH:30]=2)[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 11380407Methyl 4-iodosalicylateHCID 220003137-(1-Adamantyl)-6-benzyloxy-2-naphthylboronic acid

Product 1

HCID 22000341Methyl 2-hydroxy-4-[7-(1-adamantyl)-6-benzyloxy-2-naphthyl]benzoateYield 36.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

300 mg (8.8 mmol) of tetrakis(triphenyl-phosphine)palladium(0), 50 ml of toluene and 2.46 g (8.8 mmol) of methyl 2-hydroxy-4-iodobenzoate were introduced into a three-necked flask under a stream of nitrogen and stirring was carried out at room temperature for 20 minutes. 5.52 g (13.4 mmol) of 7-(1-adamantyl)-6-benzyloxy-2-naphthylboronic acid and 8.8 ml of an aqueous potassium carbonate solution (2N) were then added and the reaction mixture was heated at reflux for 8 hours. The reaction mixture was evaporated to dryness, the residue was taken up in water and ethyl ether and the organic phase was separated by settling, dried over magnesium sulfate and evaporated. The residue was purified by chromatography on a silica column eluted with a mixture of ethyl acetate and heptane (10/90). 1.65 g (36%) of methyl 2-hydroxy-4-[7-(1-adamantyl)-6-benzyloxy-2-naphthyl]benzoate were obtained.

Workup

  1. temperaturethe reaction mixture was heated
  2. temperatureat reflux for 8 hours
  3. customThe reaction mixture was evaporated to dryness
  4. customethyl ether and the organic phase was separated
  5. dry with materialdried over magnesium sulfate
  6. customevaporated
  7. customThe residue was purified by chromatography on a silica column
  8. washeluted with a mixture of ethyl acetate and heptane (10/90)

Sources & evidence

ORD record
ord-92ce47a1224c412093aaae3c05566aef
Source dataset
uspto-grants-1999_09
Patent number
US05952382

Reaction notes

Loading…