Ethyl Acetate → tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate

HRID 626815노트

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HRID 626815 반응식
[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=C)[C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)(=[O:3])[CH3:2].I([O-])(=O)(=O)=[O:26].[Na+].C(OCC)(=O)C>O1CCCC1.O.[Os](=O)(=O)(=O)=O>[C:1]([C:4]1[C:9]([O:10][CH2:11][CH2:12][NH:13][C:14](=[O:20])[O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[C:8]([CH:21]=[O:26])[C:7]([CH3:23])=[C:6]([Cl:24])[CH:5]=1)(=[O:3])[CH3:2]

참가 물질

7

반응물 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodate2회HCID 86697511tert-Butyl [2-(6-acetyl-4-chloro-3-methyl-2-vinylphenoxy)ethyl]carbamate

생성물 1

HCID 86697512tert-Butyl [2-(6-acetyl-4-chloro-2-formyl-3-methylphenoxy)ethyl]carbamate수율 73%

시약·촉매·용매 3

HCID 30318Osmium Tetroxide촉매2회HCID 962Water용매4회HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

tert-Butyl [2-(6-acetyl-4-chloro-3-methyl-2-vinylphenoxy)ethyl]carbamate (4.1 g, 12 mmol) was dissolved in tetrahydrofuran (300 mL) and 0.157 M osmium tetraoxide in water (10 mL) was added followed by a solution of sodium metaperiodate (7.4 g, 35 mmol) in water (20 mL). The reaction was stirred at 60° C. for 2 hours. Additional 0.157 M osmium tetraoxide in water (10 mL) and a solution of sodium metaperiodate (7.4 g, 35 mmol) in water (20 mL) were added and the mixture was heated at 60° C. for 2 more hours. The mixture was poured into ethyl acetate and washed with water, brine, dried over sodium sulfate, filtered and evaporated. Purification on silica gel using ethyl acetate in hexanes (0-12%) gave the desired compound (3.0 g, 73%) (note: elutes as 2 separate peaks in both normal and reversed phase chromatography). LCMS calculated for C17H22ClNO5Na (M+Na)+: m/z=378.1; found: 378.0.

후처리

  1. temperaturethe mixture was heated at 60° C. for 2 more hours
  2. washwashed with water, brine
  3. dry with materialdried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated
  6. customPurification on silica gel

출처 및 근거

ORD 기록
ord-dd45a77876d243b49e46b9a8a2df1e17
출처 데이터셋
uspto-grants-2016_04
특허 번호
US09309251B2

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