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Water → 4-({5-[(4-Fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol

HRID 1529580
ノート
印刷プレビュー

反応式

HRID 1529580 の反応式
[F-].C([N+](CCCC)(CCCC)CCCC)CCC.[Si]([O:26][C:27]1[CH:52]=[CH:51][C:30]([O:31][CH2:32][C:33]2[O:34][C:35]3[CH2:36][N:37]([C:42]([C:44]4[CH:49]=[CH:48][C:47]([F:50])=[CH:46][CH:45]=4)=[O:43])[CH2:38][CH2:39][C:40]=3[N:41]=2)=[CH:29][CH:28]=1)(C(C)(C)C)(C)C.O>C1COCC1>[F:50][C:47]1[CH:48]=[CH:49][C:44]([C:42]([N:37]2[CH2:38][CH2:39][C:40]3[N:41]=[C:33]([CH2:32][O:31][C:30]4[CH:29]=[CH:28][C:27]([OH:26])=[CH:52][CH:51]=4)[O:34][C:35]=3[CH2:36]2)=[O:43])=[CH:45][CH:46]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

5

反応物 3

HCID 962WaterHCID 2724141Tetrabutylammonium FluorideHCID 666088752-[(4-{[Tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine

生成物 1

HCID 569416354-({5-[(4-Fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol収率 45.2%

試薬・触媒・溶媒 1

HCID 8028
Tetrahydrofuran
溶媒
2 回

実験手順

1M solution of tetra-butylammonium fluoride in THF (0.54 mL, 0.54 mmol) was added to a stirred solution of 2-[(4-{[tert-butyl(dimethyl)silyl]oxy}phenoxy)methyl]-5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridine (264 mg, 0.36 mmol) in THF (2 mL). The mixture was stirred at room temperature for 16 hours. The mixture was treated with water and extracted with AcOEt. The organic layer was separated, dried (MgSO4), filtered and the solvents evaporated in vacuo. The crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0). The desired fractions were collected and the solvents evaporated in vacuo. The product was triturated with DIPE to yield (4-({5-[(4-fluorophenyl)carbonyl]-4,5,6,7-tetrahydro[1,3]oxazolo[5,4-c]pyridin-2-yl}methoxy)phenol (60 mg, 45% yield) as a white solid. C20H17FN2O4 1H NMR (400 MHz, CDCl3) δ ppm 2.72 (br. s., 2 H), 3.69 (br. s, 2 H), 4.78 (br.s., 2 H), 5.05 (br. s., 2 H), 5.86 (br. s., 1 H), 6.74 (d, J=8.8 Hz, 2 H), 6.86 (d, J=8.8 Hz, 2 H), 7.09-7.18 (m, 2 H), 7.43-7.51 (m, 2 H).

後処理

  1. extractionextracted with AcOEt
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvents evaporated in vacuo
  6. customThe crude product was purified by flash column chromatography (silica; AcOEt in DCM 0/100 to 100/0)
  7. customThe desired fractions were collected
  8. customthe solvents evaporated in vacuo
  9. customThe product was triturated with DIPE

出典と根拠

ORDレコード
ord-86e94b8779e9411ab76942d9053b7726
出典データセット
uspto-grants-2015_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09090632B2

反応ノート

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