Boron trifluoride etherate → Cyclododecanecarboxaldehyde

HRID 2380362

반응식

HRID 2380362 반응식
[O:1]1[C:3]2([CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]2)[CH2:2]1.B(F)(F)F.CCOCC.CCCCCC.CCCCCC.C(OCC)(=O)C>CCOCC>[CH:3]1([CH:2]=[O:1])[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1

참가 물질

6

반응물 4

HCID 8000Boron trifluoride etherateHCID 8058HexaneHCID 110198001-Oxaspiro[2.11]tetradecaneHCID 21226206Ethyl acetate hexane

생성물 1

HCID 78737Cyclododecanecarboxaldehyde수율 34%

시약·촉매·용매 1

HCID 3283Diethyl Ether용매

실험 절차

To 5.0 g (25.5 mmol) of 1-oxaspiro[2.11]tetradecane in 50 ml of dry ether at 0° C. is slowly added 1.8 ml (2.1 g, 14.6 mmol) of boron trifluoride etherate. The ice bath is removed and after 15 minutes at room temperature the solution is partitioned between ether and saturated sodium bicarbonate. The organic phase is evaporated to give a clear oil. Flash chromatography over silica gel using a hexane to hexane:ethyl acetate (9:1) gradient give 1.6 g (34%) of a clear oil: NMR (CDCl3) δ1.28-1.8 (m, 18H), 2.03 (s, 1H), 2,42 (m, 1H), 9.62 (s, 1H)

후처리

  1. customat 0° C.
  2. customThe ice bath is removed and after 15 minutes at room temperature the solution
  3. customis partitioned between ether and saturated sodium bicarbonate
  4. customThe organic phase is evaporated
  5. customto give a clear oil

출처 및 근거

ORD 기록
ord-b85d2a328a6b4358b4d5a2c29a48dbe9
출처 데이터셋
uspto-grants-1994_11
특허 번호
US05366993

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