Hydrochloric Acid → 3',4',5'-Trimethoxycinnamyl alcohol

HRID 1267622

反応式

HRID 1267622 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:11]=[C:12]([O:16][CH3:17])[C:13]=1[O:14][CH3:15])[CH:6]=[CH:7][C:8](O)=[O:9].C(Cl)(=O)OCC.[BH4-].[Na+].Cl>C1COCC1.C(N(CC)CC)C>[CH3:17][O:16][C:12]1[CH:11]=[C:5]([CH:6]=[CH:7][CH2:8][OH:9])[CH:4]=[C:3]([O:2][CH3:1])[C:13]=1[O:14][CH3:15]

参加物

7

反応物 4

HCID 313Hydrochloric AcidHCID 70213-(3,4,5-Trimethoxyphenyl)acrylic acidHCID 10928Ethyl chloroformateHCID 4311764Sodium borohydride

生成物 1

HCID 739243',4',5'-Trimethoxycinnamyl alcohol

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8471Triethylamine溶媒

実験手順

3,4,5-Trimethoxycinnamic acid (1.5 g) was dissolved in THF (100 mL), triethylamine (0.64 mL) was added to the solution under ice cooling, and ethyl chlorocarbonate (0.44 mL) was then added dropwise thereto. After stirring the resultant mixture at room temperature for 1 hour, sodium borohydride (477 mg) was added to the mixture under ice cooling. After stirring the resultant mixture at room temperature for 1 hour, diluted hydrochloric acid was added to the reaction mixture to conduct extraction with chloroform. The resultant organic layer was washed with saturated brine, dried over anhydrous sodium sulfate and then concentrated under reduced pressure. The residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1) to obtain the title compound.

後処理

  1. extractionextraction with chloroform
  2. washThe resultant organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was purified by column chromatography on silica gel (hexane:ethyl acetate=1:1)

出典と根拠

ORDレコード
ord-b1259147d3e147f487dc04a96e5576dc
出典データセット
uspto-grants-2003_04
特許番号
US06552188B2

関連ノート

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