Hydrochloric Acid → (1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

HRID 407857ノート

反応式

HRID 407857 の反応式
Br[C:2]1[CH:3]2[O:11][CH:9]([CH:10]=1)[CH:8]1[CH:4]2[C:5](=[O:22])[CH:6]([C:13]2[C:18]([CH3:19])=[CH:17][C:16]([CH3:20])=[CH:15][C:14]=2[CH3:21])[C:7]1=[O:12].[F:23][C:24]1[CH:29]=[CH:28][C:27](B(O)O)=[CH:26][CH:25]=1.O.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(OC)=CC=C(S([O-])(=O)=O)C=2OC)CCCCC1.[Na+].P([O-])([O-])([O-])=O.[K+].[K+].[K+].Cl>O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:23][C:24]1[CH:29]=[CH:28][C:27]([C:2]2[CH:3]3[O:11][CH:9]([CH:10]=2)[CH:8]2[CH:4]3[C:5](=[O:22])[CH:6]([C:13]3[C:14]([CH3:21])=[CH:15][C:16]([CH3:20])=[CH:17][C:18]=3[CH3:19])[C:7]2=[O:12])=[CH:26][CH:25]=1

参加物

8

反応物 5

HCID 313Hydrochloric AcidHCID 62657Potassium Phosphate, TribasicHCID 2856454-Fluorophenylboronic acidHCID 23693092Sodium 2'-(dicyclohexylphosphanyl)-2,6-dimethoxy(1,1'-biphenyl)-3-sulfonate--water (1/1/1)HCID 67284125(1RS, 2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione

生成物 1

HCID 67283881(1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 962Water溶媒

反応条件

温度
150 °C

実験手順

A mixture of (1RS,2RS,6SR,7SR)-8-bromo-4-(2,4,6-trimethylphenyl)-10-oxatricyclo-[5.2.1.02,6]dec-8-en-3,5-dione (300 mg, 0.82 mmol), 4-fluorophenylboronic acid (171 mg, 1.22 mmol), sodium 2′-dicyclohexylphosphino-2,6-dimethoxy-1,1-biphenyl-3-sulfonate hydrate (17 mg, 0.03 mmol), potassium phosphate (522 mg, 2.5 mmol) and palladium acetate (4 mg, 0.02 mmol) in water (8 ml) are heated for 150° C. for 25 minutes under microwave irradiation. The mixture is cooled to room temperature and dilute aqueous hydrochloric acid is added. The mixture is filtered and the filtrate is extracted with ethyl acetate. The organic extracts are combined, dried over anhydrous magnesium sulfate, filtered and the filtrate is concentrated under reduced pressure. Purification by column chromatography on silica gel gives (1RS,2SR,6RS,7RS)-8-(4-fluorophenyl)-4-(2,4,6-trimethylphenyl)-10-oxatricyclo[5.2.1.02,6]dec-8-en-3,5-dione.

後処理

  1. temperatureThe mixture is cooled to room temperature
  2. filtrationThe mixture is filtered
  3. extractionthe filtrate is extracted with ethyl acetate
  4. dry with materialdried over anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. customPurification by column chromatography on silica gel

出典と根拠

ORDレコード
ord-3cbf642752874ed7bf5be552f8d94916
出典データセット
uspto-grants-2014_06
特許番号
US08754242B2

反応ノート

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