Propargyl alcohol → [3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester

HRID 1250111ノート

反応式

HRID 1250111 の反応式
[CH2:1]([OH:4])[C:2]#[CH:3].[C:5]([O:9][C:10](=[O:20])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15](Br)[CH:14]=1)([CH3:8])([CH3:7])[CH3:6].[Cl-].[NH4+]>N1CCCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:5]([O:9][C:10](=[O:20])[CH2:11][O:12][C:13]1[CH:18]=[CH:17][CH:16]=[C:15]([C:3]#[C:2][CH2:1][OH:4])[CH:14]=1)([CH3:8])([CH3:7])[CH3:6]

参加物

6

反応物 3

HCID 7859Propargyl alcoholHCID 25517Ammonium ChlorideHCID 20577391tert-Butyl 2-(3-bromophenoxy)acetate

生成物 1

HCID 54255612[3-(3-Hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester収率 64%

試薬・触媒・溶媒 2

HCID 178418397HCID 178418397、化合物触媒HCID 31268Pyrrolidine溶媒

反応条件

温度
77.5 °C

実験手順

Tetrakis(triphenylphosphine)palladium(0) (0.66 g, 0.57 mmol) and propargyl alcohol (1.34 mL, 22.97 mmol) were added to a solution of (3-bromophenoxy) acetic acid tert-butyl ester (3.3 g, 11.49 mmol) in pyrrolidine (35 mL) under an argon atmosphere at room temperature. The mixture was heated at 75-80° C. for 2.5 hours. Excess saturated ammonium chloride was added and the mixture was extracted with diethyl ether. The extract was washed with brine, dried over sodium sulfate, and concentrated to dryness. Purification by flash chromatography, eluting with hexane/ethyl acetate, gave [3-(3-hydroxyprop-1-ynyl)phenoxy]acetic acid tert-butyl ester as a pale yellow oil (1.93 g, 64%).

後処理

  1. extractionthe mixture was extracted with diethyl ether
  2. washThe extract was washed with brine
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated to dryness
  5. customPurification by flash chromatography
  6. washeluting with hexane/ethyl acetate

出典と根拠

ORDレコード
ord-00bf84f5715d49e0afb0ce73e180434c
出典データセット
uspto-grants-2002_01
特許番号
US06335459B1

反応ノート

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