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

HRID 2056761ノート

反応式

HRID 2056761 の反応式
[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

参加物

4

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-bd734c6dfc71466c8d9a99b936348e37
出典データセット
uspto-grants-2008_02
特許番号
US07335660B2

反応ノート

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