Imidazole → 2-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethanol

HRID 470965노트

반응식

HRID 470965 반응식
[Si:1](Cl)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2].N1C=CN=C1.[OH:14][CH2:15][CH2:16][C:17]1[S:21][C:20]([CH2:22][C:23](O)=[O:24])=[CH:19][CH:18]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.O.C1COCC1>[Si:1]([O:24][CH2:23][CH2:22][C:20]1[S:21][C:17]([CH2:16][CH2:15][OH:14])=[CH:18][CH:19]=1)([C:4]([CH3:7])([CH3:6])[CH3:5])([CH3:3])[CH3:2]

참가 물질

8

반응물 4

HCID 795ImidazoleHCID 11430Potassium CarbonateHCID 28928tert-Butyldimethylsilyl chlorideHCID 579889872-(5-(2-Hydroxyethyl)thiophen-2-yl)acetic acid

생성물 1

HCID 579893142-(5-(2-(tert-Butyldimethylsilyloxy)ethyl)thiophen-2-yl)ethanol

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8028Tetrahydrofuran용매

실험 절차

tert-Butyldimethylsilyl chloride (6.63 g) was added portionwise to a solution of imidazole (2.99 g) and 2-(5-(2-hydroxyethyl)thiophen-2-yl)acetic acid (3.9 g) (example 4, step e) in DMF (50 mL) over 20 minutes. The resulting solution was stirred for 1 h. THF (50 mL) was then added and the reaction cooled in an ice bath. A solution of potassium carbonate (4.05 g) in water (50 mL) was then added and the mixture stirred for 20 min. The reaction was partitioned between ethyl acetate and brine. The organic layer was separated and washed twice with brine, dried over sodium sulphate, filtered and the solvent evaporated in vacuo. The residue was dissolved in THF (80 mL) and borane tetrahydrofuran complex (1M solution in THF, 62.8 mL) was added dropwise. The resulting solution was stirred for 2 h and quenched by dropwise addition of methanol (30 mL). The solvents were then evaporated in vacuo. Purification was by silica gel chromatography, eluting with 83:17 isohexane:ethyl acetate to give the subtitled compound as a yellow liquid. Yield 4.6 g.

후처리

  1. temperaturethe reaction cooled in an ice bath
  2. stirringthe mixture stirred for 20 min
  3. customThe reaction was partitioned between ethyl acetate and brine
  4. customThe organic layer was separated
  5. washwashed twice with brine
  6. dry with materialdried over sodium sulphate
  7. filtrationfiltered
  8. customthe solvent evaporated in vacuo
  9. dissolutionThe residue was dissolved in THF (80 mL)
  10. additionborane tetrahydrofuran complex (1M solution in THF, 62.8 mL) was added dropwise
  11. stirringThe resulting solution was stirred for 2 h
  12. customquenched by dropwise addition of methanol (30 mL)
  13. customThe solvents were then evaporated in vacuo
  14. customPurification
  15. washeluting with 83:17 isohexane

출처 및 근거

ORD 기록
ord-ab3694f9a95548e2bcb2a0e04f0529b4
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629271B2

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