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1,2-Dimethoxyethane → [4'-(Morpholin-4-yl)biphenyl-3-yl]methanol

HRID 1021214
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HRID 1021214 반응식
C(=O)([O-])[O-].[Na+].[Na+].CC1(C)C(C)(C)OB([C:15]2[CH:20]=[CH:19][C:18]([N:21]3[CH2:26][CH2:25][O:24][CH2:23][CH2:22]3)=[CH:17][CH:16]=2)O1.Br[C:29]1[CH:30]=[C:31]([CH2:35][OH:36])[CH:32]=[CH:33][CH:34]=1.COCCOC>C1C=CC([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)=CC=1.O>[N:21]1([C:18]2[CH:17]=[CH:16][C:15]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([CH2:35][OH:36])[CH:30]=3)=[CH:20][CH:19]=2)[CH2:22][CH2:23][O:24][CH2:25][CH2:26]1
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참가 물질

7

반응물 4

HCID 80711,2-DimethoxyethaneHCID 10340Sodium CarbonateHCID 851413-Bromobenzyl alcoholHCID 27953614-[4-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine

생성물 1

HCID 68308508[4'-(Morpholin-4-yl)biphenyl-3-yl]methanol수율 86.6%

시약·촉매·용매 2

HCID 178418397
HCID 178418397, 화합물
촉매
HCID 962Water용매

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온도
80 °C

실험 절차

Tetrakis(triphenylphosphine)palladium (36 mg) and sodium carbonate (330 mg) were added to a mixture of 4-[4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)phenyl]morpholine (300 mg), (3-bromophenyl)methanol (233 mg), DME (6 ml), and water (3 ml), followed by stirring at 80° C. overnight, and then the reaction mixture was concentrated under reduced pressure. Water and CHCl3 were added to the obtained residue, and the organic layer was dried over MgSO4, and then concentrated under reduced pressure. The obtained residue was purified by silica gel column chromatography (EtOAc/hexane/CHCl3) to obtain [4′-(morpholin-4-yl)biphenyl-3-yl]methanol (242 mg).

후처리

  1. concentrationthe reaction mixture was concentrated under reduced pressure
  2. additionWater and CHCl3 were added to the obtained residue
  3. dry with materialthe organic layer was dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (EtOAc/hexane/CHCl3)

출처 및 근거

ORD 기록
ord-79eb507037ee4b9fb8658186f41dedd3
출처 데이터셋
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08716470B2

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