Tetrabutylammonium Fluoride → (4-Hydroxymethyl-5-methyl-furan-2-yl)-acetic acid ethyl ester

HRID 490344노트

반응식

HRID 490344 반응식
[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][O:12][Si](C(C)C)(C(C)C)C(C)C)[CH:10]=1)[CH3:2].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[CH2:1]([O:3][C:4](=[O:24])[CH2:5][C:6]1[O:7][C:8]([CH3:23])=[C:9]([CH2:11][OH:12])[CH:10]=1)[CH3:2]

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 58824185(5-Methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acetic acid ethyl ester

생성물 1

HCID 58824186(4-Hydroxymethyl-5-methyl-furan-2-yl)-acetic acid ethyl ester수율 67.3%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

A solution of (5-methyl-4-triisopropylsilanyloxymethyl-furan-2-yl)-acetic acid ethyl ester (29) (0.5 g) in tetrahydrofuran (3.0 mL) was cooled to 0° C. with stirring and treated with tetrabutylammonium fluoride (1.0 M solution in tetrahydrofuran, 2.82 mL) under argon. After 30 minutes, the resulting solution was concentrated in-vacuo and partitioned between water (30 mL) and ethyl acetate (4×25 mL). The combined organic extracts were washed with brine (50 mL), dried (Na2SO4), filtered and concentrated in vacuo. The residue was purified by flash chromatography eluting with diethyl ether/petroleum ether (1:1 by volume) to give compound 30 as a clear oil (188 mg). LC/MS System A: Rt=2.34 mins.

후처리

  1. concentrationthe resulting solution was concentrated in-vacuo
  2. custompartitioned between water (30 mL) and ethyl acetate (4×25 mL)
  3. washThe combined organic extracts were washed with brine (50 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by flash chromatography
  8. washeluting with diethyl ether/petroleum ether (1:1 by volume)

출처 및 근거

ORD 기록
ord-19908e3c82524e45aa407567b39a0d94
출처 데이터셋
uspto-grants-2009_05
특허 번호
US07528157B2

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