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

HRID 1503384노트

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HRID 1503384 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
100 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-77a27a3ee5d24bcea20f2bbada9bbfd3
출처 데이터셋
uspto-grants-2015_12
특허 번호
US09212153B2

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