Boron trifluoride etherate → 7'-Fluoro-3',4'-dihydro-2'H-spiro[[1,3]dithiolane-2,1'-naphthalene]

HRID 919191ノート

反応式

HRID 919191 の反応式
[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]2=O)=[CH:4][CH:3]=1.B(F)(F)F.CCOCC.[CH2:22]([SH:25])[CH2:23][SH:24]>>[F:1][C:2]1[CH:11]=[C:10]2[C:5]([CH2:6][CH2:7][CH2:8][C:9]32[S:25][CH2:22][CH2:23][S:24]3)=[CH:4][CH:3]=1

参加物

4

反応物 3

HCID 8000Boron trifluoride etherateHCID 109021,2-EthanedithiolHCID 103747647-Fluoro-1,2,3,4-tetrahydronaphthalen-1-one

生成物 1

HCID 866652417'-Fluoro-3',4'-dihydro-2'H-spiro[[1,3]dithiolane-2,1'-naphthalene]収率 100%

実験手順

Dissolved 7-fluorotetralone, 51 (10.0 g, 60.9 mmol) in 1,2-ethanedithiol (10 mL) and cooled reaction to 0° C. Boron trifluoride diethyl etherate (7.5 mL) was added dropwise. The white suspension became yellow and homogenous. The wet ice bath was removed and the reaction was warmed to ambient temperature. The reaction was then diluted with heptanes (25 mL) and poured into an ice cold solution of saturated sodium bicarbonate. The organic layer was separated, dried over sodium sulfate and concentrated to give colorless oil (14.69 g, 60.9 mmol, 100% yield). 1H NMR (400 MHz, CDCl3) δ: 7.60 (d, J=12 Hz, 1H), 6.94 (t, J=4 Hz, 1H), 6.84 (t, J=8 Hz, 1H), 3.56 (m, 2H), 3.46 (m, 2H), 2.75 (m, 2H), 2.37 (m, 2H), 1.99 (m, 2H).

後処理

  1. temperaturecooled
  2. customreaction to 0° C
  3. customThe wet ice bath was removed
  4. additionThe reaction was then diluted with heptanes (25 mL)
  5. additionpoured into an ice cold solution of saturated sodium bicarbonate
  6. customThe organic layer was separated
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-704e6a99e18f480d99efc16815b3c75a
出典データセット
uspto-grants-2016_03
特許番号
US09273009B2

反応ノート

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