Sodium hydride → 5'-bromo-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one

HRID 472968ノート

反応式

HRID 472968 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2([OH:21])[CH2:16][CH2:15][C:14]3[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=3[CH2:12][CH2:11]2)=[O:9])[CH:7]=1.[H-].[Na+]>C1COCC1>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[O:21][C:10]3([CH2:16][CH2:15][C:14]4[CH:17]=[CH:18][CH:19]=[CH:20][C:13]=4[CH2:12][CH2:11]3)[C:8](=[O:9])[C:6]=2[CH:7]=1

参加物

4

反応物 2

HCID 24758Sodium hydrideHCID 58197198(5-bromo-2-fluorophenyl)(7-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)methanone

生成物 1

HCID 581970305'-bromo-5,6,8,9-tetrahydro-3'H-spiro[benzo[7]annulene-7,2'-benzofuran]-3'-one収率 71%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A mixture of (5-bromo-2-fluorophenyl)(7-hydroxy-6,7,8,9-tetrahydro-5H-benzo[7]annulen-7-yl)methanone (1.3739 g, 3.78 mmol) and 60% NaH (0.5900 g, 14.75 mmol) in THF (20 mL) was heated at 100° C. for 1 h. The reaction mixture was then cooled with an ice bath and quenched with 2 N HCl (5 mL), extracted with ethyl acetate, dried over Na2SO4. After the solvents were evaporated, the residue was purified by chromatography on silica gel eluted with hexanes/ethyl acetate to afford 0.9170 g (71%) of 5′-bromo-5,6,8,9-tetrahydro-3′H-spiro[benzo[7]annulene-7,2′-benzofuran]-3′-one as a solid. LC-MS tR=2.31 min in 3 min chromatography, m/z 343, 345 (MH+); 1H NMR (400 MHz, CDCl3) δ 7.79-7.78 (m, 1H), 7.73-7.71 (m, 1H), 7.17 (m, 4H), 7.11-7.09 (m, 1H), 3.41-3.35 (m, 2H), 2.78-2.75 (m, 2H), 1.95-1.85 (m, 4H); 13C NMR (100 MHz, CDCl3) δ 201.53, 169.46, 141.50, 140.56, 128.93, 127.47, 126.62, 121.63, 115.61, 114.15, 92.58, 32.98, 29.67.

後処理

  1. temperatureThe reaction mixture was then cooled with an ice bath
  2. customquenched with 2 N HCl (5 mL)
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customAfter the solvents were evaporated
  6. customthe residue was purified by chromatography on silica gel
  7. washeluted with hexanes/ethyl acetate

出典と根拠

ORDレコード
ord-f4fcb6df23d847469257e37130d425e9
出典データセット
uspto-grants-2014_01
特許番号
US08633212B2

反応ノート

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