Iodine → 1-[4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]propan-2-ol

HRID 1023326

반응식

HRID 1023326 반응식
Br[C:2]1[CH:16]=[CH:15][C:5]([CH2:6][O:7][Si:8]([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9])=[CH:4][CH:3]=1.II.[O:19]1[CH:21]([CH3:22])[CH2:20]1.[NH4+].[Cl-]>C1COCC1>[Si:8]([O:7][CH2:6][C:5]1[CH:15]=[CH:16][C:2]([CH2:20][CH:21]([OH:19])[CH3:22])=[CH:3][CH:4]=1)([C:11]([CH3:14])([CH3:13])[CH3:12])([CH3:10])[CH3:9]

참가 물질

6

반응물 4

HCID 807IodineHCID 6378Propylene OxideHCID 25517Ammonium ChlorideHCID 108595834-Bromobenzyloxy-tert-butyldimethylsilane

생성물 1

HCID 673770301-[4-({[Tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]propan-2-ol

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
50 °C

실험 절차

To a solution of (4-bromobenzyloxy)(tert-butyl)dimethylsilane (3.080 g) in THF (20 mL) were added Mg (0.288 g) and I2 (cat) at room temperature under an Ar atmosphere. The mixture was heated at 50° C. for 1 hour, and then cooled to room temperature. To the mixture was added 1,2-epoxypropane (0.77 mL) at room temperature under an Ar atmosphere, and the mixture was stirred at room temperature for 14.5 hours, and then heated at 50° C. for 1 hour, and then cooled to room temperature. To the mixture was added saturated aqueous NH4Cl, and the mixture was extracted with AcOEt. The organic layer was washed with saturated aqueous NaCl, dried over anhydrous Na2SO4, and concentrated under reduced pressure. The residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1) to afford 1-[4-({[tert-butyl(dimethyl)silyl]oxy}methyl)phenyl]propan-2-ol (1.485 g) as a colorless oil.

후처리

  1. temperaturecooled to room temperature
  2. temperatureheated at 50° C. for 1 hour
  3. temperaturecooled to room temperature
  4. extractionthe mixture was extracted with AcOEt
  5. washThe organic layer was washed with saturated aqueous NaCl
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was purified by silica gel column chromatography (n-hexane/AcOEt=2/1)

출처 및 근거

ORD 기록
ord-3bbe2a901c9b43e794b12ea9324b81fc
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722663B2

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