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

HRID 626815ノート

反応式

HRID 626815 の反応式
[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]

参加物

7

反応物 3

HCID 8857Ethyl AcetateHCID 23667635Sodium periodate2 回HCID 86697511tert-Butyl [2-(6-acetyl-4-chloro-3-methyl-2-vinylphenoxy)ethyl]carbamate

生成物 1

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

試薬・触媒・溶媒 3

HCID 30318Osmium Tetroxide触媒2 回HCID 962Water溶媒4 回HCID 8028Tetrahydrofuran溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-dd45a77876d243b49e46b9a8a2df1e17
出典データセット
uspto-grants-2016_04
特許番号
US09309251B2

反応ノート

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