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

HRID 45466
ノート
印刷プレビュー

反応式

HRID 45466 の反応式
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
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-7143236d711a4fbeb76e6c15d3763690
出典データセット
uspto-grants-2013_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08541522B2

反応ノート

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