Tetrabutylammonium Fluoride → 3-{[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

HRID 2056761노트

반응식

HRID 2056761 반응식
[Si]([O:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:32]3[CH2:36][CH2:35][O:34][C:33]3=[O:37])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1)(C(C)(C)C)(C1C=CC=CC=1)C1C=CC=CC=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[OH:18][CH2:19][CH2:20][C@H:21]1[C:26]2[CH:27]=[CH:28][C:29]([CH2:31][N:32]3[CH2:36][CH2:35][O:34][C:33]3=[O:37])=[CH:30][C:25]=2[CH2:24][CH2:23][O:22]1

참가 물질

4

반응물 2

HCID 2724141Tetrabutylammonium FluorideHCID 693083913-{[(1S)-1-(2-{[tert-Butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

생성물 1

HCID 693084103-{[(1S)-1-(2-Hydroxyethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a stirred solution of 3-{[(1S)-1-(2-{[tert-butyl(diphenyl)silyl]oxy}ethyl)-3,4-dihydro-1H-2-benzopyran-6-yl]methyl}-1,3-oxazolidin-2-one (0.22 g, 0.43 mmol) in dry THF (30 ml) was added tetrabutylammonium fluoride (1M solution in THF) (0.51 mL, 0.51 mmol) and the reaction stirred at room temperature under nitrogen over the weekend. The reaction was quenched by addition of water and extracted with dichloromethane. The combined organic extracts were dried (MgSO4), filtered and evaporated in vacuo. The crude product was purified by flash chromatography on silica, eluting with methanol/dichloromethane (1:9), to yield the title compound as a colourless oil.

후처리

  1. customThe reaction was quenched by addition of water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined organic extracts were dried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe crude product was purified by flash chromatography on silica
  7. washeluting with methanol/dichloromethane (1:9)

출처 및 근거

ORD 기록
ord-bd734c6dfc71466c8d9a99b936348e37
출처 데이터셋
uspto-grants-2008_02
특허 번호
US07335660B2

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