Hydrochloric Acid → (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile

HRID 973517ノート

反応式

HRID 973517 の反応式
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:14]=[CH:13][C:12]([CH2:15][C:16]#[N:17])=[CH:11][CH:10]=2)=[CH:5][CH:4]=1.[Li]CCCC.[O:23]1[C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24]1.Cl>O1CCCC1.CCCCCC.CN(P(N(C)C)(N(C)C)=O)C>[OH:23][C@H:25]([CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH3:31])[CH2:24][CH:15]([C:12]1[CH:13]=[CH:14][C:9]([C:6]2[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=2)=[CH:10][CH:11]=1)[C:16]#[N:17]

参加物

8

反応物 4

HCID 313Hydrochloric AcidHCID 1620686(2R)-2-HexyloxiraneHCID 15733995(4'-Methoxy[1,1'-biphenyl]-4-yl)acetonitrileHCID 178418339Butyllithium

生成物 1

HCID 54327812(4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile収率 65%

試薬・触媒・溶媒 3

HCID 8028Tetrahydrofuran溶媒2 回HCID 8058Hexane溶媒HCID 12679Hexamethylphosphoramide溶媒

実験手順

To a solution of 1.02 g (4.6 mmol) of 4-(4-methoxyphenyl)phenylacetonitrile in 40 ml of tetrahydrofuran (THF) was added, at -78° C., 1.5 M n-BuLi solution in hexane in an amount of 3.6 ml (5.5 mmol). This mixture was stirred for 1 hour. Thereto were added a solution of 705 mg (5.5 mmol) of (R)-1,2-epoxyoctane in 20 ml of THF and 5 ml of HMPA. The resulting mixture was warmed to room temperature, and then stirred overnight. The reaction mixture was neutralized with 3 M hydrochloric acid, and then subjected to extraction with 300 ml of ethyl acetate. The resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution, dried with anhydrous magnesium sulfate, filtered, and then concentrated. The residue was separated and purified by column chromatography (hexane/ethyl acetate=3/1), thereby obtaining 1.05 g (yield 65%) of (4R)-4-hydroxy-2-[4-(4-methoxyphenyl)phenyl]decanenitrile.

後処理

  1. stirringstirred overnight
  2. extractionsubjected to extraction with 300 ml of ethyl acetate
  3. washThe resulting ethyl acetate solution was washed with saturated sodium chloride aqueous solution
  4. dry with materialdried with anhydrous magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was separated
  8. custompurified by column chromatography (hexane/ethyl acetate=3/1)

出典と根拠

ORDレコード
ord-e54df340496945618826c3278ce6295b
出典データセット
uspto-grants-1991_11
特許番号
US05064564

反応ノート

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