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

HRID 973517노트

반응식

HRID 973517 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매HCID 12679Hexamethylphosphoramide용매

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-e54df340496945618826c3278ce6295b
출처 데이터셋
uspto-grants-1991_11
특허 번호
US05064564

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