Chlorodicyclohexylphosphine → 2-(Dicyclohexylphosphino)-2'-methoxybiphenyl

HRID 227861

반응식

HRID 227861 반응식
CC1C=[CH:6][C:5]([CH:8]([C:14]2[CH:19]=[CH:18][C:17](C)=[CH:16][CH:15]=2)[C:9](=[O:13])[CH:10]([CH3:12])C)=CC=1.[Li][CH2:22]CCC.Cl[P:27]([CH:34]1[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]1)[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1>C1COCC1>[CH:28]1([P:27]([CH:34]2[CH2:39][CH2:38][CH2:37][CH2:36][CH2:35]2)[C:19]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[C:8]2[CH:5]=[CH:6][CH:12]=[CH:10][C:9]=2[O:13][CH3:22])[CH2:33][CH2:32][CH2:31][CH2:30][CH2:29]1

참가 물질

5

반응물 3

HCID 2734135ChlorodicyclohexylphosphineHCID 120407443-Methyl-1,1-bis(4-methylphenyl)-2-butanoneHCID 178418339Butyllithium

생성물 1

HCID 117941862-(Dicyclohexylphosphino)-2'-methoxybiphenyl수율 54.4%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

A solution of 1 (535 mg, 2.03 mmol) in THF (20 mL) was cooled to −78° C. under argon, then n-BuLi (1.6 M in hexane, 1.35 mL, 2.16 mmol) was added dropwise. After 2.5 h at −78° C., a solution of chlorodicyclohexylphosphine (570 mg, 2.45 mmol) in THF (3 mL) was added over 10 min. The reaction mixture was then allowed to warm to room temperature overnight, then quenched with saturated aqueous NaHCO3 and concentrated in vacuo. The resulting aqueous suspension was extracted with ether (2×50 mL), and the combined ethereal layers were dried (Na2SO4), filtered and concentrated in vacuo. The resulting crude solid was recrystallized from ethanol to afford 420 mg (54%) of a white solid.

후처리

  1. customquenched with saturated aqueous NaHCO3
  2. concentrationconcentrated in vacuo
  3. extractionThe resulting aqueous suspension was extracted with ether (2×50 mL)
  4. dry with materialthe combined ethereal layers were dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe resulting crude solid was recrystallized from ethanol

출처 및 근거

ORD 기록
ord-2f074a422ab7469abcd2a49f5192b14d
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07560582B2

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