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

HRID 655077

반응식

HRID 655077 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 21881883Oxolane--water (1/1)용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-66880a3a91f5458492c6643a8c152417
출처 데이터셋
uspto-grants-2011_12
특허 번호
USRE043006E1

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