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Benzyl Bromide → 1-[4'-(4-Benzyloxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid

HRID 1528769
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인쇄 미리보기

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HRID 1528769 반응식
C([O:3][C:4]([C:6]1([C:9]2[CH:14]=[CH:13][C:12]([C:15]3[CH:20]=[CH:19][C:18]([C:21]4[O:25][N:24]=[C:23]([CH3:26])[C:22]=4[CH2:27][OH:28])=[CH:17][CH:16]=3)=[CH:11][CH:10]=2)[CH2:8][CH2:7]1)=[O:5])C.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.[H-].[Na+]>O1CCOCC1>[CH2:29]([O:28][CH2:27][C:22]1[C:23]([CH3:26])=[N:24][O:25][C:21]=1[C:18]1[CH:19]=[CH:20][C:15]([C:12]2[CH:13]=[CH:14][C:9]([C:6]3([C:4]([OH:3])=[O:5])[CH2:7][CH2:8]3)=[CH:10][CH:11]=2)=[CH:16][CH:17]=1)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1
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참가 물질

5

반응물 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 665772181-[4'-(4-Hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester

생성물 1

HCID 665785371-[4'-(4-Benzyloxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid

시약·촉매·용매 1

HCID 312751,4-Dioxane용매

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온도
60 °C

실험 절차

1-[4′-(4-Hydroxymethyl-3-methyl-isoxazol-5-yl)-biphenyl-4-yl]-cyclopropanecarboxylic acid ethyl ester (0.100 g, 0.265 mmol) and benzyl bromide (0.031 mL, 0.265 mmol) were dissolved in dioxane. Sodium hydride (60% in mineral oil, 0.016 g, 0.398 mmol) was added and the reaction was heated to 60° C. overnight. Upon cooling the reaction was partitioned between EtOAc and H2O, acidified with 1 N HCl (aq.) and extracted with EtOAc. After drying the residue was purified by silica gel chromatography (EtOAc/hexanes) to afford the title compound.

후처리

  1. temperatureUpon cooling the reaction
  2. customwas partitioned between EtOAc and H2O
  3. extractionextracted with EtOAc
  4. customAfter drying the residue
  5. customwas purified by silica gel chromatography (EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-c2f1a6e704db4734a4ecf6dd4cf838ff
출처 데이터셋
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09090573B2

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