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

HRID 969481

반응식

HRID 969481 반응식
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

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 178420554HCID 178420554, 화합물촉매HCID 962Water용매HCID 80711,2-Dimethoxyethane용매

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온도
80 °C

실험 절차

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-hydroxybenzeneboronic 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%.

후처리

  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

출처 및 근거

ORD 기록
ord-1dfe92e2a34c44d4891e5ed515bff36e
출처 데이터셋
uspto-grants-2007_12
특허 번호
US07307078B2

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