Propargyl alcohol → HCID 59736985, 화합물

HRID 252813

반응식

HRID 252813 반응식
Br[C:2]1[CH:3]=[CH:4][C:5]([N+:9]([O-:11])=[O:10])=[C:6]([NH2:8])[CH:7]=1.[CH2:12]([OH:15])[C:13]#[CH:14]>COCCOC.C(N(CC)CC)C.ClCCl.[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cu]I>[NH2:8][C:6]1[CH:7]=[C:2]([C:14]#[C:13][CH2:12][OH:15])[CH:3]=[CH:4][C:5]=1[N+:9]([O-:11])=[O:10]

참가 물질

8

반응물 2

HCID 7859Propargyl alcoholHCID 53147665-Bromo-2-nitroaniline

생성물 1

HCID 59736985HCID 59736985, 화합물수율 83%

시약·촉매·용매 5

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)촉매HCID 11979704Tetrakis(triphenylphosphine)palladium촉매HCID 6344Dichloromethane용매HCID 80711,2-Dimethoxyethane용매HCID 8471Triethylamine용매

실험 절차

A suspension of bromoarene 2 (447 mg g; 2.06 mmol); tetrakis(triphenylphosphine) palladium(0) (145 mg, 0.12 mmol) and copper(I)iodide (143 mg, 0.75 mmol) in degassed ethyleneglycol dimethylether (2.5 mL) and triethylamine (1.5 mL), was stirred at room temperature under nitrogen in the dark for 10 min and then treated with neat prop-2-yn-1-ol (0.7 mL, 12 mmol) (or any other alkyne of choice, 5 eq.), and the mixture stirred under the same conditions for 48 h, diluted with dichloromethane (50 mL), filtered through a celite pad and concentrated. Purification by flash chromatography (eluent 50 to 75% AcOEt in hexane) afforded compound 72 (328 mg, 83% yield).

후처리

  1. filtrationfiltered through a celite pad
  2. concentrationconcentrated
  3. customPurification by flash chromatography (eluent 50 to 75% AcOEt in hexane)

출처 및 근거

ORD 기록
ord-00ed007235bd4f8d9c3b37583f62e169
출처 데이터셋
uspto-grants-2011_01
특허 번호
US07868205B2

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