Potassium Carbonate → Tert-butyl(4'-hydroxybiphenyl-3-ylmethyl)methylcarbamate

HRID 1245433

反応式

HRID 1245433 の反応式
C(=O)([O-])[O-].[K+].[K+].Br[C:8]1[CH:9]=[C:10]([CH:21]=[CH:22][CH:23]=1)[CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16].[OH:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1>COCCOC.O.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[OH:24][C:25]1[CH:30]=[CH:29][C:28]([C:8]2[CH:23]=[CH:22][CH:21]=[C:10]([CH2:11][N:12]([CH3:20])[C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:9]=2)=[CH:27][CH:26]=1

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27343604-Hydroxyphenylboronic acidHCID 20738487tert-Butyl 3-bromobenzyl(methyl)carbamate

生成物 1

HCID 69643261Tert-butyl(4'-hydroxybiphenyl-3-ylmethyl)methylcarbamate収率 68%

試薬・触媒・溶媒 3

HCID 178420554HCID 178420554、化合物触媒HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

反応条件

温度
80 °C

実験手順

41.6 ml (83.2 mmol) of aqueous 2M potassium carbonate solution are added dropwise to a solution of 10 g (33 mmol) of tert-butyl (3-bromobenzyl)-N-methylcarbamate and 8.3 g (60 mmol) of 4-hydroxy-benzeneboronic acid in 100 ml of ethylene glycol dimethyl ether. The reaction medium is degassed and 1.9 g (1.7 mmol) of tetrakis(triphenylphosphino)palladium are added. After heating for 12 hours at 80° C., the reaction medium is cooled, diluted with water and extracted with ethyl acetate. The organic phase is dried over sodium sulfate, filtered and concentrated under vacuum. The residue obtained is purified by chromatography on a column of silica eluted with an 80/20 heptane/ethyl acetate mixture. 7 g of tert-butyl (4′-hydroxybiphenyl-3-ylmethyl)methylcarbamate are obtained in the form of a beige-colored solid, in a yield of 68%.

後処理

  1. customThe reaction medium is degassed
  2. temperaturethe reaction medium is cooled
  3. extractionextracted with ethyl acetate
  4. dry with materialThe organic phase is dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated under vacuum
  7. customThe residue obtained
  8. customis purified by chromatography on a column of silica
  9. washeluted with an 80/20 heptane/ethyl acetate mixture

出典と根拠

ORDレコード
ord-c975fdabc7054d1cbd61c63116e3ad1c
出典データセット
uspto-grants-2006_10
特許番号
US07125869B2

関連ノート

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