Diiodomethane → Betaxolol

HRID 1765493

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HRID 1765493 반응식
[CH2:1]([O:4][CH2:5][CH2:6][C:7]1[CH:21]=[CH:20][C:10]([O:11][CH2:12][CH:13]([OH:19])[CH2:14][NH:15][CH:16]([CH3:18])[CH3:17])=[CH:9][CH:8]=1)[CH:2]=[CH2:3].[CH2:22]([Zn]CC)C.ICI.[Cl-].[NH4+]>C1(C)C=CC=CC=1>[CH3:18][CH:16]([NH:15][CH2:14][CH:13]([OH:19])[CH2:12][O:11][C:10]1[CH:20]=[CH:21][C:7]([CH2:6][CH2:5][O:4][CH2:1][CH:2]2[CH2:22][CH2:3]2)=[CH:8][CH:9]=1)[CH3:17]

참가 물질

6

반응물 4

HCID 6346DiiodomethaneHCID 25517Ammonium ChlorideHCID 116593381-{4-[2-(Allyloxy)-ethyl]phenoxy}-3-isopropylamino propan-2-olHCID 178418750HCID 178418750, 화합물

생성물 1

HCID 2369Betaxolol

시약·촉매·용매 1

HCID 1140Toluene용매

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온도
0 °C

실험 절차

To a stirred solution of compound of formula (1) (1 g, 0.003 mol) in dry toluene (5 ml), diethylzinc (1.1 M solution in toluene, 14 ml, 0.017 mol) was added at 0° C. under nitrogen atmosphere followed by diiodomethane (1.38 ml, 0.017 mol). The reaction was stirred for 16 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 toluene. The combined organic layer was washed with a solution of sodium thiosulphate, dried over anhydrous sodium sulphate, filtered and concentrated to yield racemic betaxolol of formula (2) 1.6 g (84%) mp 70 –72° C. as a white solid.

후처리

  1. customThe organic layer was separated
  2. extractionthe aqueous layer extracted repeatedly with toluene
  3. washThe combined organic layer was washed with a solution of sodium thiosulphate
  4. dry with materialdried over anhydrous sodium sulphate
  5. filtrationfiltered
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-d4a41da84d1d4cb7a3440d8420287f4f
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07227039B2

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