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

HRID 919191노트

반응식

HRID 919191 반응식
[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

참가 물질

4

반응물 3

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

생성물 1

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

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-704e6a99e18f480d99efc16815b3c75a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273009B2

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