Diiodomethane → 1-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

HRID 1745866노트

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HRID 1745866 반응식
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][C:10]([O:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:9][CH:8]=1)[CH:2]=[CH2:3].I[CH2:22]I.[Cl-].[NH4+]>CCCCCC.C([Zn]CC)C>[CH2:14]([O:13][C:10]1[CH:11]=[CH:12][C:7]([CH2:6][CH2:5][O:4][CH2:1][CH:2]2[CH2:22][CH2:3]2)=[CH:8][CH:9]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

참가 물질

6

반응물 3

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 22227278HCID 22227278, 화합물

생성물 1

HCID 115146971-[2-(Cyclopropylmethoxy)ethyl]-4-(phenylmethoxy)benzene

시약·촉매·용매 2

HCID 8058Hexane용매HCID 178418750HCID 178418750, 화합물용매

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온도
0 °C

실험 절차

To a stirred solution of compound of formula (7), (12 g, 0.0447 mol) in dry hexane (50 ml), diethyl zinc (1.1 M solution in hexane, 185 ml) was added at 0° C. under nitrogen atmosphere followed by diiodomethane (18 ml, 0.224 mol). The reaction was stirred for 6 h at 0° C. and poured over cold aqueous solution of ammonium chloride. The organic layer was separated and the aqueous layer extracted repeatedly with diethyl ether. The combined organic layer was washed with aq. solution of sodium thiosulphate, dried over anhydrous sodium sulphate, filtered and concentrated. The crude product was purified over silica gel column using ethyl acetate and light petroleum ether (1:50) as an eluent to afford compound of formula (8), as a colorless liquid 11.365 g (90%).

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted repeatedly with diethyl ether
  3. washThe combined organic layer was washed with aq. solution of sodium thiosulphate
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude product was purified over silica gel column

출처 및 근거

ORD 기록
ord-5954218747e140378d0ce94f946ceb2b
출처 데이터셋
uspto-grants-2006_03
특허 번호
US07019172B2

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