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Triphenylphosphine → tert-Butyl [2-(6-acetyl-2-bromo-4-chloro-3-methylphenoxy)ethyl]carbamate

HRID 626813
ノート
印刷プレビュー

反応式

HRID 626813 の反応式
[Br:1][C:2]1[C:3]([OH:13])=[C:4]([C:10](=[O:12])[CH3:11])[CH:5]=[C:6]([Cl:9])[C:7]=1[CH3:8].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.O[CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40].N(C(OC(C)C)=O)=NC(OC(C)C)=O>C(Cl)Cl.O>[C:10]([C:4]1[C:3]([O:13][CH2:34][CH2:35][NH:36][C:37](=[O:43])[O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[C:2]([Br:1])[C:7]([CH3:8])=[C:6]([Cl:9])[CH:5]=1)(=[O:12])[CH3:11]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 4

HCID 11776TriphenylphosphineHCID 75555Diisopropyl diazene-1,2-dicarboxylateHCID 2733206tert-butyl N-(2-hydroxyethyl)carbamateHCID 120274791-(3-Bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone

生成物 1

HCID 86697510tert-Butyl [2-(6-acetyl-2-bromo-4-chloro-3-methylphenoxy)ethyl]carbamate収率 59.8%

試薬・触媒・溶媒 2

HCID 962Water溶媒
HCID 6344Dichloromethane溶媒

反応条件

温度
0 °C

実験手順

A suspension of 1-(3-bromo-5-chloro-2-hydroxy-4-methylphenyl)ethanone (8.0 g, 30 mmol) in methylene chloride (304 mL) was heated with a heat gun to dissolve the solids and cooled to 0° C. To the mixture was added triphenylphosphine (11 g, 43 mmol) and tert-butyl (2-hydroxyethyl)carbamate (9.4 mL, 61 mmol). Diisopropyl azodicarboxylate (8.4 mL, 43 mmol) was added dropwise. The mixture was stirred for 23 hours at room temperature. The reaction mixture was poured into water and extracted with methylene chloride. The organic layer was separated, washed with brine, dried with sodium sulfate, filtered, and concentrated. The oil was dissolved in methylene chloride and was purified on silica using ethyl acetate in hexanes (0-25%) to give the desired compound (7.3 g, 59%). LCMS calculated for C16H21BrClNO4Na (M+Na)+: m/z=428.0, 430.0; found: 428.0, 430.0.

後処理

  1. temperaturewas heated with a heat gun
  2. dissolutionto dissolve the solids
  3. extractionextracted with methylene chloride
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. dissolutionThe oil was dissolved in methylene chloride
  10. customwas purified on silica

出典と根拠

ORDレコード
ord-31a60cafc84c48d59dddfa917fe02efa
出典データセット
uspto-grants-2016_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09309251B2

反応ノート

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このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート