Boron trifluoride etherate → Cyclododecanecarboxaldehyde

HRID 2380362

反応式

HRID 2380362 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 78737Cyclododecanecarboxaldehyde収率 34%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

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)

後処理

  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

出典と根拠

ORDレコード
ord-b85d2a328a6b4358b4d5a2c29a48dbe9
出典データセット
uspto-grants-1994_11
特許番号
US05366993

関連ノート

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