Imidazole → (E)-3-[2(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid

HRID 655077

反応式

HRID 655077 の反応式
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11].[CH3:13][C:14]([Si:17](Cl)([CH3:19])[CH3:18])([CH3:16])[CH3:15].N1C=CN=C1.[Li+].[OH-]>CN(C=O)C.C1COCC1.O>[C:14]([Si:17]([CH3:19])([CH3:18])[O:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1/[CH:8]=[CH:9]/[C:10]([OH:12])=[O:11])([CH3:16])([CH3:15])[CH3:13]

参加物

7

反応物 4

HCID 795ImidazoleHCID 3939Lithium HydroxideHCID 28928tert-Butyldimethylsilyl chlorideHCID 637540O-Coumaric Acid

生成物 1

HCID 22290462(E)-3-[2(tert-Butyl-dimethyl-silanoxy)-phenyl]-acrylic acid収率 53.9%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 21881883Oxolane--water (1/1)溶媒

実験手順

To a solution of 8.2 g of (E)-3-(2-hydroxy-phenyl)-acrylic acid and 15.2 g of TBDMS-Cl in 10 ml of DMF was added 11.9 g of imidazole and the mixture was stirred at room temperature for 24 h. After aqueous work-up, the bis-silylated product was saponified with 2.1 g of LiOH in THF-H2O for 0.5 h at 0° C. The mixture was concentrated in vacuo and TBDMS-OH removed by extraction with hexane. The aqueous layer was acidified to pH 4 with KHSO4 and extracted with EtOAc. The organic phases were washed with brine, dried (Na2SO4) and evaporated to dryness. The semi-solid residue was suspended in hexane, filtered and the filtrate evaporated to dryness to yield 7.5 g of a pale yellow oil, which solidified upon standing.

後処理

  1. concentrationThe mixture was concentrated in vacuo and TBDMS-OH
  2. customremoved by extraction with hexane
  3. extractionextracted with EtOAc
  4. washThe organic phases were washed with brine
  5. dry with materialdried (Na2SO4)
  6. customevaporated to dryness
  7. filtrationfiltered
  8. customthe filtrate evaporated to dryness

出典と根拠

ORDレコード
ord-66880a3a91f5458492c6643a8c152417
出典データセット
uspto-grants-2011_12
特許番号
USRE043006E1

関連ノート

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