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Ammonium Chloride → (2-(Benzyloxy)-3-tert-butylphenyl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol

HRID 45466
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HRID 45466 반응식
Br[C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1.C([Li])CCC.[CH2:21]([O:28][C:29]1[C:34]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39]([C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:40])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.[Cl-].[NH4+]>O1CCCC1>[CH2:21]([O:28][C:29]1[C:34]([C:35]([CH3:38])([CH3:37])[CH3:36])=[CH:33][CH:32]=[CH:31][C:30]=1[C:39]([C:2]1[CH:3]=[C:4]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[O:14][CH3:15])[CH:5]=[CH:6][CH:7]=1)([C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][CH:46]=1)[OH:40])[C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1
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참가 물질

6

반응물 4

HCID 25517Ammonium ChlorideHCID 186686213'-Bromo-2-methoxybiphenylHCID 58238504(2-(Benzyloxy)-3-tert-butylphenyl)(phenyl)methanoneHCID 178418339Butyllithium

생성물 1

HCID 58238592(2-(Benzyloxy)-3-tert-butylphenyl)(2'-methoxybiphenyl-3-yl)(phenyl)methanol수율 60%

시약·촉매·용매 1

HCID 8028
Tetrahydrofuran
용매
2회

실험 절차

A solution of 3′-bromo-2-methoxybiphenyl (1 g, 3.8 mmol) in anhydrous tetrahydrofuran (15 mL) was stirred at −78° C. and 2.5M n-butyllithium in hexanes (1.6 mL, 4 mmol) was added at such a rate that the temperature did not exceed −70° C. Stirring was continued at −78° C. for 1 hr. A solution of (2-(benzyloxy)-3-tert-butylphenyl)(phenyl)methanone (1.3 g, 3.8 mmol) in tetrahydrofuran (5 mL) was added at such a rate that the temperature did not exceed −65° C. The reaction mixture was allowed to reach room temperature slowly and was poured onto saturated ammonium chloride (100 mL) and extracted with ethyl acetate (150 mL). The organic extract was washed with water (2×80 mL). The organic layer was dried over sodium sulfate, filtered and the solvent was removed on a rotary evaporator. The crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (3.5 L). Pure 29 (1.2 g, 60%) was isolated.

후처리

  1. customdid not exceed −70° C
  2. customdid not exceed −65° C
  3. customto reach room temperature
  4. extractionextracted with ethyl acetate (150 mL)
  5. extractionThe organic extract
  6. washwas washed with water (2×80 mL)
  7. dry with materialThe organic layer was dried over sodium sulfate
  8. filtrationfiltered
  9. customthe solvent was removed on a rotary evaporator
  10. customThe crude product was purified by chromatography on silica (80 g) with 2% ethyl acetate in heptane (3.5 L)

출처 및 근거

ORD 기록
ord-7143236d711a4fbeb76e6c15d3763690
출처 데이터셋
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08541522B2

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