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

HRID 618481ノート

反応式

HRID 618481 の反応式
[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]

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-92ce47a1224c412093aaae3c05566aef
出典データセット
uspto-grants-1999_09
特許番号
US05952382

反応ノート

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