Triphenylphosphine → HCID 70495691、化合物

HRID 523337

反応式

HRID 523337 の反応式
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:11]=[CH:10][C:9]([OH:12])=[CH:8][CH:7]=1.[Br:14][CH:15](O)[CH2:16][CH3:17].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Br:14][CH2:15][CH2:16][CH2:17][O:12][C:9]1[CH:10]=[CH:11][C:6](/[CH:5]=[CH:4]/[C:3]([O:2][CH3:1])=[O:13])=[CH:7][CH:8]=1

参加物

6

反応物 4

HCID 11776TriphenylphosphineHCID 92203Methyl p-coumarateHCID 5363146Diisopropyl azodicarboxylateHCID 12887879Bromopropanol

生成物 1

HCID 70495691HCID 70495691、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution 5 g (28.1 mmol) of 4-Hydroxycinnamic acid methyl ester, 4.9 g (35.1 mmol) of 4 bromopropanol, 9.2 g (35.1 mmol) of triphenylphosphine in 100 mL of THF are added 7.1 g (35.1 mmol) of diisopropylazodicarboxylate under inert atmosphere. The solution is heated up to reflux and allowed to stir overnight. After 20 hours, the reaction mixture is partitioned between EtOAc and water. The organic phase is washed repeatedly with water, dried over sodium sulphate, filtered and concentrated by rotary evaporation to give 7.5 g of (methyl (2E)-3-[4-(3-bromopropoxy)phenyl]prop-2-enoate.

後処理

  1. temperatureThe solution is heated up
  2. temperatureto reflux
  3. waitAfter 20 hours
  4. customthe reaction mixture is partitioned between EtOAc and water
  5. washThe organic phase is washed repeatedly with water
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated by rotary evaporation

出典と根拠

ORDレコード
ord-db9adabeb650425a934951281dbbebef
出典データセット
uspto-grants-2016_05
特許番号
US09334366B2

関連ノート

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